Water → alpha-Cyano-4-fluoro-3-phenoxybenzyl methanesulfonate

HRID 28095노트

반응식

HRID 28095 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].[CH2:22]([N:24](CC)CC)C.O>CCOCC>[CH3:17][S:18]([O:7][CH:6]([C:22]#[N:24])[C:5]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1)(=[O:20])=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1100684-Fluoro-3-phenoxybenzaldehyde

생성물 1

HCID 23338840alpha-Cyano-4-fluoro-3-phenoxybenzyl methanesulfonate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

The cyanohydrin of 4-fluoro-3-phenoxybenzaldehyde (0.038 mol) is dissolved in 150 ml ether and cooled to 0° in an ice bath. To this is slowly added methanesulfonyl chloride in 20 ml ether. The mixture is stirred for 10 minutes then triethylamine in 20 ml ether is added dropwise. The solution turns white, and a precipitate appears. The reaction mixture is kept at 0° over-night and is then worked up with water and extracted with ether. The ether phase is washed with 30% sodium bisulfite solution (2×), ether and water (2×), and dried over sodium sulfate. The mixture is filtered and the filtrate concentrated to give α-cyano-4 fluoro-3-phenoxybenzyl methanesulfonate.

후처리

  1. temperaturecooled to 0° in an ice bath
  2. waitThe reaction mixture is kept at 0° over-night
  3. extractionextracted with ether
  4. washThe ether phase is washed with 30% sodium bisulfite solution (2×), ether and water (2×)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture is filtered
  7. concentrationthe filtrate concentrated

출처 및 근거

ORD 기록
ord-12863afc3be7445787ba457a06f1e1ba
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225533

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