1,3-Dichloroacetone → 4-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole

HRID 1296548Notes

Reaction equation

HRID 1296548 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][C:14]([NH2:16])=[O:15].[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:16]=[C:14]([CH:13]=[CH:12][C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=2[F:1])[O:15][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 691109983-(2-Fluoro-4-trifluoromethyl-phenyl)-acrylamide

Product 1

HCID 690723654-Chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazoleYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.00 g (17.1 mmol) 3-(2-Fluoro-4-trifluoromethyl-phenyl)-acrylamide, 2.60 g (21.3 mmol) 1,3-dichloroacetone and 40 ml toluene were kept at reflux temperature for 16 h with continuous removal of water by use of a Dean-Stark trap. After cooling to room temperature, two extractions with 100 ml water, the organic phase was dried over sodium sulphate and the solvent removed in vacuo. Chromatography on silica gel (eluent: n-heptane/ethyl acetate 5:1) gave 1.20 g (23%) 4-chloromethyl-2-[2-(2-fluoro-4-trifluoromethyl-phenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 16 h
  2. customwith continuous removal of water by use of a Dean-Stark trap
  3. extractiontwo extractions with 100 ml water
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1cfc118b2707439f9b1bbec70e5c47f8
Source dataset
uspto-grants-2007_07
Patent number
US07247649B2

Reaction notes

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