Phosgene → (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride

HRID 1419553Notes

Reaction equation

HRID 1419553 reaction equation
S(Cl)(Cl)=O.[C:5]([Cl:8])(Cl)=[O:6].[F:9][CH:10]([F:25])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([CH:22]([CH3:24])[CH3:23])C(O)=O)=[CH:14][CH:13]=1>>[F:9][CH:10]([F:25])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([CH:22]([CH3:23])[CH3:24])[C:5]([Cl:8])=[O:6])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 24386Thionyl ChlorideHCID 13118566(S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid

Product 1

HCID 53862600(S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride

Procedure

Add 1-3 moles of thionyl chloride or phosgene into (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid, and allow the mixture to react at 10° C. to reflux temperature of the solvent for 0.1-100 hours, preferably for 1-5 hours. After the reaction is completed, distill off the unreacted thionyl chloride or phosgene to give the (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride.

Workup

  1. customto react at 10° C.
  2. temperatureto reflux temperature of the solvent for 0.1-100 hours
  3. distillationdistill off the unreacted thionyl chloride or phosgene

Sources & evidence

ORD record
ord-7fc57907f8bc49e58a5fa23c35366488
Source dataset
uspto-grants-1999_03
Patent number
US05886207

Reaction notes

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