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

HRID 28095Notes

Reaction equation

HRID 28095 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-12863afc3be7445787ba457a06f1e1ba
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

Loading…