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

HRID 869894Notes

Reaction equation

HRID 869894 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.S(Cl)([Cl:20])=O.CN(C)C=O>>[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 3

HCID 6228DimethylformamideHCID 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

Procedure

To 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (18.8 g, 78.0 mmol) in thionyl chloride (17.0 mL, 233 mmol) was added N,N-dimethylformamide (200 μL, 2.6 mmol). The reaction mixture was stirred at room temperature for 2 hours. Excess thionyl chloride and N,N-dimethylformamide were removed in vacuo and the resulting acid chloride was used directly in next step.

Workup

  1. customExcess thionyl chloride and N,N-dimethylformamide were removed in vacuo

Sources & evidence

ORD record
ord-3c3787294281411baf4b6977abe37dcc
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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