p-Tolyl methyl sulfone → 4-(Methylsulfonyl)benzyl Bromide

HRID 747386

반응식

HRID 747386 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([CH3:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:10][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH2:11][Br:12])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

참가 물질

4

반응물 2

HCID 18521p-Tolyl methyl sulfoneHCID 67184N-bromobutanimide

생성물 1

HCID 27335814-(Methylsulfonyl)benzyl Bromide수율 94.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

Methyl p-tolyl sulfone (24 g, 0.14 mol) in 550 ml CCl4 was heated to reflux temperature, N-bromosuccinimide (17.8 g, 0.14 mol) was added in portions and the mixture was refluxed for 3 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to yield 4-methanesulfonylbenzyl bromide as a crystalline solid (32.9 g), 1H-NMR (CDCl3) δ 8.05 (d, 2H), 7.70 (d, 2H), 4.45 (s, 2H), 3.09 (s, 3H). To the crude product in water (200 ml) were added sodium sulfite (33.2 g, 264 mmol) and tetrabutylammonium bromide (0.41 g, 1.64 mmol), and the mixture was refluxed for 2 h. After cooling to room temperature the solution was extracted with ethyl acetate, the aqueous phase was then concentrated to half the volume and cooled. The precipitate was filtered off and dried under vacuum at 70° C. to yield sodium 4-methanesulfonyl-benzylsulfonate (33.3 g, quant.).

후처리

  1. additionwas added in portions
  2. temperaturethe mixture was refluxed for 3 h
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-e689fc2b7d38400f92aa962ebb42ddc4
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396846B2

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