Dimethyl Sulfide → Dimethyl-2,6-difluorophenacylsulfonium bromide

HRID 1981321

반응식

HRID 1981321 반응식
[Br:1]Br.[CH3:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13])=[O:5].[CH3:14][S:15][CH3:16]>ClCCl.C(OCC)C>[Br-:1].[CH3:14][S+:15]([CH3:16])[CH2:3][C:4]([C:6]1[C:7]([F:13])=[CH:8][CH:9]=[CH:10][C:11]=1[F:12])=[O:5]

참가 물질

6

반응물 3

HCID 1068Dimethyl SulfideHCID 24408BromineHCID 836431-(2,6-Difluorophenyl)ethan-1-one

생성물 1

HCID 20265451Dimethyl-2,6-difluorophenacylsulfonium bromide수율 38%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A solution of bromine (4.1 ml, 80 mmoles) in dichloromethane (6 ml) was added dropwise to a solution of 2,6-difluoroacetophenone (12.4 g, 80 mmoles) in anhydrous diethyl ether (100 ml). the reaction solution was evaporated and the resulting liquid was dissolved in tetrahydrofuran (150 ml) and methyl sulfide (9 ml, 120 mmoles) was added. The mixture was allowed to stand at room temperature for 6 days (approximately 144 hours). The crystals were filtered to yield 8.9 g (38%) of dimethyl-2,6-difluorophenacylsulfonium bromide. A mixture of the sulfonium salt (8.9 g) and isopropyl nitrate (6.4 ml, 60 mmoles) was stirred in dichloromethane (80 ml) for 7 days (approximately 168 hours) at room temperature. The volatiles were evaporated and the residue was dissolved in diethyl ether (250 ml). The organic solution was washed 4 times with 100 ml portions of water, saturated sodium chloride, dried (sodium sulfate), and evaporated to give 6.8 g of a solid. Recrystallization from carbon tetrachloride (250 ml) gave 4.9 g (23%) of crystals, melting point 138°-140° C.

후처리

  1. customthe reaction solution was evaporated
  2. dissolutionthe resulting liquid was dissolved in tetrahydrofuran (150 ml)
  3. custom(approximately 144 hours)
  4. filtrationThe crystals were filtered

출처 및 근거

ORD 기록
ord-cda81d32f60248b6a47f63c6fce966a0
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04514410

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