1,3-Dichloroacetone → HCID 22241447, compound

HRID 1397347Notes

Reaction equation

HRID 1397347 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1[N:13]=[C:11]([C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([F:7])[CH:9]=2)[O:12][CH:5]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 680003-Fluorobenzamide

Product 1

HCID 22241447HCID 22241447, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1,3-Dichloroacetone (3.65 g, 28.75 mmol) was added to a solution of 3-fluorobenzamide (2 g, 14.37 mmol) in dry toluene (20 mL). The resulting reaction mixture was stirred at 100° C. for 5 h. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether) to afford 4-(chloromethyl)-2-(3-fluorophenyl)oxazole (1.2 g, yield 39%) as a yellow liquid. NMR (300 MHz, CDCl3) δ 7.85-7.83 (m, 1H), 7.77-7.73 (m, 2H), 7.48-7.41 (m, 1H), 7.20-7.14 (m, 1H), 4.58 (d, J=0.9 Hz, 2H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f2457d88c5a546b69bd2f950fdf0ab55
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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