tert-Butylsulfinamide, (S)-(-)- → HCID 87096337, compound

HRID 2196345Notes

Reaction equation

HRID 2196345 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([C:8](=O)[CH:9]([F:11])[F:10])[CH:7]=1.[C:14]([S@@:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6](/[C:8](=[N:20]/[S:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:19])/[CH:9]([F:11])[F:10])[CH:7]=1

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 548578331-(5-Bromo-2-fluorophenyl)-2,2-difluoroethanone

Product 1

HCID 87096337HCID 87096337, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 1140TolueneSolvent

Procedure

To the mixture of 1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-ethanone (6.0 kg, 23.7 mol) and (S)-(−)-tert-butanesulfinamide (3.3 kg, 27.2 mol) were added toluene (73 L) with stirring at ambient temperature. After 5 min, titanium ethoxide (6.5 kg, 28.5 mol) was added and the mixture was heated to 50˜55° C. The mixture was stirred at 50˜55° C. for 3 h and allowed to cool to ambient temperature before concentration in vacuo. The resulting crude product was used directly in next chemical transformation without further purification. ESIMS: 356 [(M+H)+].

Workup

  1. temperaturethe mixture was heated to 50˜55° C
  2. stirringThe mixture was stirred at 50˜55° C. for 3 h
  3. temperatureto cool to ambient temperature before concentration in vacuo
  4. customThe resulting crude product was used directly in next chemical transformation without further purification

Sources & evidence

ORD record
ord-8327cf61f9db47ca934b3ef0681778a6
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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