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

HRID 716615Notes

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-5b4d5db001af4bb2bb0aa66fe357455a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09192606B2

Reaction notes

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