Bromide ion → (2-Chloro-4-methoxybenzyl)(triphenyl)phosphonium bromide

HRID 11084

반응식

HRID 11084 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10]O.[BrH:12].[Br-].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C.C(Cl)Cl.C1C=CC=CC=1>[Br-:12].[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 259Bromide ionHCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 14771756(2-Chloro-4-methoxyphenyl)methanol

생성물 1

HCID 87899044(2-Chloro-4-methoxybenzyl)(triphenyl)phosphonium bromide수율 100%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 23443464Methane, dichloro-, compd. with benzene (1:1)용매

실험 절차

Bromination of (2-chloro-4-methoxyphenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the reaction time for the bromination was 4 h and the reaction time for the displacement was 28 h, gave the phosphonium salt (574) (100%) as a white solid, mp (CH2Cl2/benzene) 223–226° C. 1H NMR (CDCl3) δ 7.82–7.61 (m, 15H), 7.53 (dd, J=8.4, 2.7 Hz, 1H), 6.72 (d, J=2.8 Hz, 1H), 6.70 (dd, J=8.9, 2.5 Hz, 1H), 5.57 (d, J=13.6 Hz, 2H), 3.74 (s, 3H). Found: C, 63.05; H, 4.74. C26H23BrClOP requires C, 62.73; H, 4.66.

후처리

  1. waitthe reaction time for the displacement was 28 h

출처 및 근거

ORD 기록
ord-b0cc435ca11b4dacb9b6522a9e461fa6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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