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

HRID 1020451Notes

Reaction equation

HRID 1020451 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

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 442061031-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarboxylic acid

Product 1

HCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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

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

Sources & evidence

ORD record
ord-c0feb6ca6d6a4688836f620d46f8d544
Source dataset
uspto-grants-2014_05
Patent number
US08716338B2

Reaction notes

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