3-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acid → 3-(4-Chloro-phenyl)-isoxazol-4-ylmethanol

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](O)=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.FC1C=CC(C2C(C(O)=O)=CON=2)=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acid

HCID 289494543-(4-Chlorophenyl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 684443823-(4-Chloro-phenyl)-isoxazol-4-ylmethanolYield 46.1%

Procedure

As described for example 323e, 3-(4-chloro-phenyl)-isoxazole-4-carboxylic acid (40.0 g, 178.9 mmol) was converted, instead of 3-(4-fluoro-phenyl)-isoxazole-4-carboxylic acid, to the title compound (17.3 g, 46%) which was obtained as a light green solid. MS: m/e=210.1 [M+H]+.

Sources & evidence

ORD record: ord-c9b7205302664f39b32962d0525827d4
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518974B2

Reaction notes

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