Oxalyl chloride → 4-(Difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carbonyl chloride

HRID 1843056Notes

Reaction equation

[F:1][CH:2]([F:19])[C:3]1[C:8]([C:9](O)=[O:10])=[CH:7][N:6]=[C:5]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[N:4]=1.C(Cl)(=O)C([Cl:23])=O>ClCCl.CN(C)C=O>[F:1][CH:2]([F:19])[C:3]1[C:8]([C:9]([Cl:23])=[O:10])=[CH:7][N:6]=[C:5]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In 10 ml of dichloromethane, 467 mg of 4-(difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylic acid are admixed with two drops of N,N-dimethylformamide and cooled to 0° C. Following the dropwise addition of 167 μl of oxalyl chloride, the reaction mixture is stirred at room temperature for three hours and then concentrated by evaporation. This gives the crude product 4-(difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carbonyl chloride.

Workup

concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-8dd05b45fa9347e3abbf331a6b713599
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946234B2

Reaction notes

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