1,3-Dichloroacetone → HCID 29062595, compound

HRID 1397427Notes

Reaction equation

HRID 1397427 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O>CCOC(C)=O>[Cl:11][CH2:12][C:13]1[N:6]=[C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[O:5][CH:15]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 679642-Fluorobenzamide

Product 1

HCID 29062595HCID 29062595, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-fluorobenzamide (500 mg, 3.59 mmol) and 1,3-dichloroacetone (1.82 g, 14.36 mmol) was heated to 130° C. for 2 h in a sealed tube. The reaction mixture was diluted with EtOAc and washed with water and brine. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 2-3% EtOAc in petroleum ether) to afford 4-(chloromethyl)-2-(2-fluorophenyl)oxazole (500 mg, yield 66%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.08-8.02 (td, J=7.6 Hz, 1.6 Hz, 1H), 7.78 (s, 1H), 7.50-7.43 (m, 1H), 7.28-7.18 (m, 2H), 4.61 (d, J=0.7 Hz, 2H). MS (ESI) m/z: Calculated for C10H7ClFNO: 211.02. found: 211.9 (M+H)+.

Workup

  1. washwashed with water and brine
  2. customSolvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 2-3% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-cae39ed95bf04fe18b5815bb42595ef0
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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