Dimethyl Sulfide → Dimethyl-2,6-difluorophenacylsulfonium bromide

HRID 463898

反応式

HRID 463898 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 20265451Dimethyl-2,6-difluorophenacylsulfonium bromide収率 38%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2aaa0e8df56e4065ba11a7362bf3e362
出典データセット
uspto-grants-1985_10
特許番号
US04544753

関連ノート

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