4-Fluorobenzoyl chloride → (4-Fluorophenyl)-2-thiazolylmethanone

HRID 2267393Notes

Reaction equation

HRID 2267393 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C[Si](C)(C)[C:13]1[S:14][CH:15]=[CH:16][N:17]=1>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 5884532-Trimethylsilylthiazole

Product 1

HCID 2758956(4-Fluorophenyl)-2-thiazolylmethanoneYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-fluorobenzoyl chloride (3 mL, 25.4 mmol) was added to 2-(trimethylsilyl)thiazole (2 mL, 12.7 mmol) in dichloromethane (70 mL). The reaction mixture was stirred over night at rt. Dichloromethane was evaporated under reduced pressure, and the crude product purified on a normal phase silica-gel column with 0-40% ethyl acetate in hexane to afford the title compound as white amorphous solid (2.050 g, 77% yield); MS (M+H)+ 208.

Workup

  1. customDichloromethane was evaporated under reduced pressure
  2. customthe crude product purified on a normal phase silica-gel column with 0-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-39c22c79ae9b4a3ab1cd2e8f25e943bf
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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