Thionyl Chloride → 1-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride

HRID 82338Notes

Reaction equation

[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14](O)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.O=S(Cl)[Cl:20]>C1(C)C=CC=CC=1>[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([Cl:20])=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(2,2-difluoro-1,3-benzodioxol-5-yl)-cyclopropanecarboxylic acid (1.2 eq) is slurried in toluene (2.5 vol) and the mixture heated to 60° C. SOCl2 (1.4 eq) is added via addition funnel. The toluene and SOCl2 are distilled from the reaction mixture after 30 minutes. Additional toluene (2.5 vol) is added and distilled again.

Workup

distillationThe toluene and SOCl2 are distilled from the reaction mixture after 30 minutes
additionAdditional toluene (2.5 vol) is added
distillationdistilled again

Sources & evidence

ORD record: ord-5d511b9e88804d278f9d465f9c28903e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846718B2

Reaction notes

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