Benzoyl Peroxide → Methyl 3-(bromomethyl)-4-chlorobenzoate

HRID 1612413노트

반응식

HRID 1612413 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 7015786Benzoic acid, 4-chloro-3-methyl-, methyl ester

생성물 1

HCID 12144656Methyl 3-(bromomethyl)-4-chlorobenzoate수율 53%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
90 °C

실험 절차

To a suspension of methyl 4-chloro-3-methylbenzoate I (19.9 g, 108 mmol) and N-bromosuccinimide (NBS, 20.2 g, 114 mmol) in carbon tetrachloride (500 mL) was added benzoyl peroxide (1.30 g, 5.4 mmol), and the mixture was stirred at 90° C. overnight. The mixture was then cooled and the white precipitate was removed by filtration. The filtrate was concentrated and the resulting solid was re-crystallized from ethyl acetate to give methyl 3-bromomethy-4-chlorobenzoate II (15.0 g, 57 mmol, 53%) as a white solid:

후처리

  1. temperatureThe mixture was then cooled
  2. customthe white precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe resulting solid was re-crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-ca51339b91794e9bb0489f2b0a42d2fc
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992215B2

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