Oxalyl chloride → 3-(2-Fluorophenyl)-isoxazole-5-carbonyl Chloride

HRID 516441Notes

Reaction equation

HRID 516441 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:18]=C(C(O)=O)O[N:15]=1>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:18]=[C:2]([C:1]([Cl:6])=[O:5])[O:3][N:15]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 31602553-(2-Fluorophenyl)-1,2-oxazole-5-carboxylic acid

Product 1

HCID 867051403-(2-Fluorophenyl)-isoxazole-5-carbonyl ChlorideYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (0.07 mL, 0.74 mmol) was added dropwise to a stirred solution of 3-(2-fluorophenyl)isoxazole-5-carboxylic acid (77 mg, 370 μmol) in THF (10 mL). The mixture was stirred at room temperature for 2 hours, then concentrated to yield the title compound (79 mg), which was used without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-b310e7e1b1c148e69bb2336af585ff11
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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