Abstract
1-Arylethanones and related compounds are brominated in dioxane with the H2 O2 -HBraq system, resulting in the replacement of two hydrogen atoms in the methyl group with
bromine. The reaction is also accompanied by bromination of the aromatic ring provided
that the latter contains electron-donating substituents. The reaction proceeds rapidly
(20 min) and results in complete conversion of ketones to give 2,2-dibromo-1-arylethanones
in yields up to 86%.
Key words
acetophenones - 1-arylethanones - 2,2-dibromo-1-arylethanones - bromination - hydrogen
peroxide
References
<A NAME="RP08705SS-1">1 </A>
Kim K.
Cho J.
Yoon SC.
J. Chem. Soc., Perkin Trans. 1
1995,
253
<A NAME="RP08705SS-2">2 </A>
Maglioli P.
de Lucchi O.
Delogu G.
Valle G.
Tetrahedron: Asymmetry
1992,
3:
365
<A NAME="RP08705SS-3">3 </A>
Nemeryuk MP.
Likhovidova MM.
Mitsev ID.
Safonova TS.
Chem. Heterocycl. Compd. (Engl. Transl.)
1986,
22:
468 ; Khim. Geterotsikl. Soedin . 1986 , 22, 566
<A NAME="RP08705SS-4">4 </A>
Araki S.
Hirashita T.
Shimizu K.
Ikeda T.
Butsugan Y.
Tetrahedron
1996,
52:
2803
<A NAME="RP08705SS-5">5 </A>
Furukawa J.
Matsumura A.
Matsuoka Y.
Kiji J.
Bull. Chem. Soc. Jpn.
1976,
49:
829
<A NAME="RP08705SS-6">6 </A>
Kawabata N.
Fujii T.
Naka M.
Yamashita S.
Bull. Chem. Soc. Jpn.
1977,
50:
1005
<A NAME="RP08705SS-7">7 </A>
Kowalski CJ.
Reddy RE.
J. Org. Chem.
1992,
57:
7194
<A NAME="RP08705SS-8">8 </A>
Kowalski CJ.
Fields KW.
J. Am. Chem. Soc.
1982,
104:
321
<A NAME="RP08705SS-9">9 </A>
Shchepin VV.
Gladkova GE.
Russkikh NYu.
J. Org. Chem. USSR (Engl. Transl.)
1992,
28:
902 ; Zh. Org. Khim . 1992 , 28 , 1156
<A NAME="RP08705SS-10">10 </A>
Zhdankin VV.
Stang PJ.
Tetrahedron Lett.
1993,
34:
1461
<A NAME="RP08705SS-11">11 </A>
Ding Y.
Huang X.
Heteroat. Chem.
2003,
14:
304
<A NAME="RP08705SS-12">12 </A>
Gololobov YuG.
Kolodka TV.
Oganesyan AS.
Chernega AN.
Antipin MYu.
Struchkov YuT.
Petrovsky PV.
J. Gen. Chem. USSR (Engl. Transl.)
1986,
56:
1512 ; Zh. Obshch. Khim . 1986 , 56 , 1708
<A NAME="RP08705SS-13">13 </A>
Boeykens M.
de Kimpe N.
Tetrahedron
1994,
50:
12349
<A NAME="RP08705SS-14">14 </A>
Ahluwalia VK.
Mehta B.
Rawat M.
Synth .Commun.
1992,
22:
2697
<A NAME="RP08705SS-15">15 </A>
Ghiaci M.
Asghari J.
Bull. Chem. Soc. Jpn.
2001,
74:
1151
<A NAME="RP08705SS-16">16 </A>
Batanero B.
Pastor G.
Barba F.
Acta Chem. Scand.
1999,
53:
910
<A NAME="RP08705SS-17">17 </A>
Rodygin MYu.
Mikhailov VA.
Savelova VA.
Russ. J. Org. Chem. (Engl. Transl.)
1994,
30:
881 ; Zh. Org. Khim . 1994 , 30 , 827
<A NAME="RP08705SS-18">18 </A>
Taylor W.
J. Chem. Soc.
1937,
304
<A NAME="RP08705SS-19">19 </A>
Kajigaeshi S.
Kakinami T.
Tokiyama H.
Hirakawa T.
Okamoto T.
Bull. Chem. Soc. Jpn.
1987,
60:
2667
<A NAME="RP08705SS-20">20 </A>
Paul S.
Gupta V.
Gupta R.
Loupy A.
Tetrahedron Lett.
2003,
44:
439
<A NAME="RP08705SS-21">21 </A>
Arutyunyan VS.
Kochikyan TV.
Egiazaryan NS.
Avetisyan AA.
Russ. J. Org. Chem.
1995,
31:
90 ; Zh. Org. Khim. 1995 , 31 , 100
<A NAME="RP08705SS-22">22 </A>
Rudakova NI.
Erykalov YuG.
Zharikova SM.
Dmitrieva EV.
Mataradze MS.
Russ. J. Gen. Chem.
1995,
65:
271 ; Zh. Obshch. Khim. 1995 , 65 , 315
<A NAME="RP08705SS-23">23 </A>
Barhate NB.
Gajare AS.
Wakharkar RD.
Bedekar AV.
Tetrahedron
1999,
55:
11127
<A NAME="RP08705SS-24">24 </A>
Barhate NB.
Gajare AS.
Wakharkar RD.
Bedekar AV.
Tetrahedron Lett.
1998,
39:
6349
<A NAME="RP08705SS-25">25 </A>
Rudakova NI.
Anufrieva OV.
Smirnova EA.
J. Gen. Chem. USSR (Engl. Transl.)
1992,
62:
1887 ; Zh. Obshch. Khim. 1992 , 62 , 2290
<A NAME="RP08705SS-26">26 </A>
Bora U.
Bose G.
Chaudhuri MK.
Dhar SS.
Gopinath R.
Khan AT.
Patel BK.
Org. Lett.
2000,
2:
247
<A NAME="RP08705SS-27">27 </A>
Espenson JH.
Zhu Z.
Zauche TH.
J. Org. Chem.
1999,
64:
1191
<A NAME="RP08705SS-28">28 </A>
Lazarev IM.
Nedolya NA.
Russ. J. Org. Chem. (Engl. Transl.)
2000,
36:
1758 ; Zh. Org. Khim. 2000 , 36 , 1811
<A NAME="RP08705SS-29">29 </A>
Dakka J.
Sasson Y.
J. Chem. Soc., Chem. Commun.
1987,
1421
<A NAME="RP08705SS-30">30 </A>
Bhatkhande BS.
Adhikari MV.
Samant SD.
Ultrason. Sonochem.
2002,
9:
31
<A NAME="RP08705SS-31">31 </A>
Vyas PV.
Bhatt AK.
Ramachandraiah G.
Bedekar AV.
Tetrahedron Lett.
2003,
44:
4085
<A NAME="RP08705SS-32">32 </A>
Narender N.
Mohan KVVK.
Reddy RV.
Srinivasu P.
Kulkarni SJ.
Raghavan KV.
J. Mol. Catal. A: Chem.
2003,
192:
73
<A NAME="RP08705SS-33">33 </A>
Jerzy G.
Slavomir Z.
Synth. Commun.
1997,
27:
3291
<A NAME="RP08705SS-34">34 </A>
Bezodis P.
Hanson JR.
Petit P.
J. Chem. Res., Synop.
1996,
7:
334
<A NAME="RP08705SS-35">35 </A>
Andrievskii AM.
Gorelik MV.
Avidon SV.
Al’tman ES.
Russ. J. Org. Chem. (Engl. Transl.)
1993,
29:
1519 ; Zh. Org. Khim . 1993 , 29 , 1828
<A NAME="RP08705SS-36">36 </A>
Hanson JR.
Opakunle A.
Petit P.
J. Chem. Res., Synop.
1995,
11:
457
<A NAME="RP08705SS-37">37 </A>
Tillu VH.
Shinde PD.
Bedekar AV.
Wakharkar RD.
Synth. Commun.
2003,
33:
1399
<A NAME="RP08705SS-38">38 </A>
Terent’ev AO.
Khodykin SV.
Troitskii NA.
Ogibin YuN.
Nikishin GI.
Synthesis
2004,
2845
<A NAME="RP08705SS-39">39 </A>
Aston JG.
Newkirk JD.
Dorsky J.
Jenkins DM.
J. Am. Chem. Soc.
1942,
64:
1413
<A NAME="RP08705SS-40">40 </A>
Kröhnke F.
Chem. Ber.
1936,
69:
921
<A NAME="RP08705SS-41">41 </A>
Magen S.
Oren J.
Fuchs B.
Tetrahedron Lett.
1984,
25:
3369
<A NAME="RP08705SS-42">42 </A>
Myddleton WW.
Barrett AW.
Seager JH.
J. Am. Chem. Soc.
1930,
52:
4410
<A NAME="RP08705SS-43">43 </A>
Smith MB.
March J.
Advanced Organic Chemistry
5th ed.:
John Wiley & Sons;
New York:
2001.
<A NAME="RP08705SS-44">44 </A>
Berliner EJ.
J. Chem. Educ.
1966,
43:
124
<A NAME="RP08705SS-45">45 </A>
Rappe C.
Acta Chem. Scand.
1968,
22:
219
<A NAME="RP08705SS-46">46 </A>
Sharma VB.
Jain SL.
Sain B.
Synlett
2005,
173
<A NAME="RP08705SS-47">47 </A>
Taylor R.
Electrophilic Aromatic Substitution
John Wiley & Sons;
New York:
1990.
<A NAME="RP08705SS-48">48 </A>
Traven’ VF.
Smrchek VA.
Stepanov BI.
J. Org. Chem. USSR (Engl. Transl.)
1973,
9:
585 ; Zh. Org. Khim . 1973 , 9 , 576
<A NAME="RP08705SS-49">49 </A>
Krawez VP.
Chervenyuk GI.
Grinev GV.
J. Org. Chem. USSR (Engl. Transl.)
1966,
2:
1238 ; Zh. Org. Khim . 1966 , 2 , 1244
<A NAME="RP08705SS-50">50 </A>
Rosenmund P.
Chem. Ber.
1957,
90:
1922
<A NAME="RP08705SS-51">51 </A>
Rutherford S.
J. Am. Chem. Soc.
1955,
77:
3278
<A NAME="RP08705SS-52">52 </A>
Yoon SC.
Cho J.
Kim K.
J. Chem. Soc., Perkin Trans. 1
1998,
109
<A NAME="RP08705SS-53">53 </A>
Tajana A.
Rossi S.
Salvaterra M.
Arzneim.-Forsch.
1971,
21:
1661
<A NAME="RP08705SS-54">54 </A>
Koziara A.
Mloykowska B.
Majewski P.
Sledzinski B.
Zwierzak A.
Pol. J. Chem.
1981,
55:
399
<A NAME="RP08705SS-55">55 </A>
Malinowski R.
Legocki J.
Pol. J. Chem.
1979,
53:
925
