Ethyl 3-(4-fluorophenyl)-1,2-oxazole-4-carboxylate → 3-(4-Chlorophenyl)-1,2-oxazole-4-carboxylic acid

HRID 83436Notes

Reaction equation

HRID 83436 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][O:9][CH:10]=1)=[O:5])C.C(OC(C1C(C2C=CC(F)=CC=2)=NOC=1)=O)C>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 743179Ethyl 3-(4-fluorophenyl)-1,2-oxazole-4-carboxylateHCID 871629Ethyl 3-(4-chlorophenyl)-1,2-oxazole-4-carboxylate

Product 1

HCID 289494543-(4-Chlorophenyl)-1,2-oxazole-4-carboxylic acidYield 100.1%

Procedure

As described for example 323d, 3-(4-chloro-phenyl)-isoxazole-4-carboxylic acid ethyl ester (57.0 g, 226.5 mmol) was converted, instead of 3-(4-fluoro-phenyl)-isoxazole-4-carboxylic acid ethyl ester, to the title compound (50.7 g, 92%) which was obtained as a light yellow solid. MS: m/e=222.3 [M−H]−.

Sources & evidence

ORD record
ord-d2b627edc96f4e359d66e0a045b2d9ee
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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