Thionyl Chloride → (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride

Reaction equation

S(Cl)([Cl:3])=O.[F:5][CH:6]([F:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([CH:18]([CH3:20])[CH3:19])[C:15](O)=[O:16])=[CH:10][CH:9]=1>>[F:5][CH:6]([F:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([CH:18]([CH3:20])[CH3:19])[C:15]([Cl:3])=[O:16])=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 13118566(S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid

Product 1

HCID 53862600(S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chlorideYield 95.2%

Procedure

Add 32.8 g (0.275 mole) of thionyl chloride to 42 g (0.17 mole) of the obtained (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid, heat with stirring under reflux for 2 hours, and then distill off the unreacted thionyl chloride to give 42.5 g of (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyryl chloride.

Workup

temperatureheat
temperatureunder reflux for 2 hours
distillationdistill off the unreacted thionyl chloride

Sources & evidence

ORD record: ord-6f561ca782dc4f628d828dcc9a745be0
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05886207

Reaction notes

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