Chlorobenzene → 1-(4-(Bromomethyl)-2-chlorophenyl)ethanone

HRID 516968

반응식

HRID 516968 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].ClC1C=CC=CC=1.[Br:19]N1C(=O)CCC1=O>C1(C)C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:9](=[O:11])[CH3:10])=[C:2]([Cl:1])[CH:7]=1

참가 물질

6

반응물 3

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 155609491-(2-Chloro-4-methylphenyl)ethanone

생성물 1

HCID 898539141-(4-(Bromomethyl)-2-chlorophenyl)ethanone수율 70%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 1140Toluene용매

반응 조건

온도
142.5 °C

실험 절차

A mixture of 1-(2-chloro-4-methylphenyl)ethanone (1.6 g, 9.50 mmol) (preparation 15) and chlorobenzene (60 ml) was prepared at room temperature and N-bromosuccinimide (NBS) (1.86 g, 10.44 mmol) added followed by a catalytic amount of benzoyl peroxide (ca. 1.5 mg, 0.005 mmol), and the resulting mixture was heated to 140-145° C. for 16 h. The mixture was then allowed to cool to room temperature, diluted with toluene (50 ml) and filtered through a celite pad. The pad was washed with toluene (2×50 ml) and the filtrate concentrated under reduced pressure and purified by column chromatography (0-10% EtOAc/Hexanes) to afford 1-(4-(bromomethyl)-2-chlorophenyl)ethanone (1.65 g, 6.65 mmol, 70%) as a yellow oil.

후처리

  1. customwas prepared at room temperature
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a celite pad
  4. washThe pad was washed with toluene (2×50 ml)
  5. concentrationthe filtrate concentrated under reduced pressure
  6. custompurified by column chromatography (0-10% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-63c8c2c23ef14ab3a813d19d099ced27
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115088B2

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