Dimethylformamide → trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride

HRID 2164853Notes

Reaction equation

HRID 2164853 reaction equation
[F:1][C:2]([F:12])=[CH:3][C@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].CN(C)C=O.C(Cl)(=O)C([Cl:21])=O>C(OCC)C>[F:1][C:2]([F:12])=[CH:3][C@H:4]1[C@H:6]([C:7]([Cl:21])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67736179trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86740007trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A stirred solution of trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (2.0 g; 0.0114 mole) and N,N-dimethylformamide (0.08 g) in 20 ml of dry diethyl ether was cooled to 0° C. A solution of oxalyl chloride (2.17 g; 0.017 mole) in 2 ml of dry diethyl ether was added to the reaction mixture during a 20 minute period. Upon complete addition the mixture was allowed to warm to room temperature and stir for two hours. The mixture was concentrated under reduced pressure to give a yellow oil. The oil was dissolved in 5 ml of dry diethyl ether and the solvent removed under reduced pressure to yield trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride as an oil.

Workup

  1. additionUpon complete addition the mixture
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a yellow oil
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4ded09a2eda446c19f6a01db7f6929b9
Source dataset
uspto-grants-1985_03
Patent number
US04507317

Reaction notes

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