5-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole → 3-(4-Fluorophenyl)-5-(trifluoromethyl)-1,2-oxazole

HRID 1521119

Reaction equation

HRID 1521119 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:14]([F:17])([F:16])[F:15])(O)[O:10][N:9]=2)=[CH:4][CH:3]=1.C1(C2CC(O)(C(F)(F)F)ON=2)C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:14]([F:16])([F:15])[F:17])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 28809765-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazoleHCID 28815383-(4-Fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol

Product 1

HCID 7992143-(4-Fluorophenyl)-5-(trifluoromethyl)-1,2-oxazoleYield 98%

Procedure

As described for example 128b, rac-3-(4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol (35.6 g, 142.9 mmol), instead of 3-phenyl-5-hydroxy-5-(trifluoromethyl)isoxazoline, was converted to the title compound (32.2 g, 98%) which was obtained as a light brown solid. MS: m/e=298.1 [M+H]+.

Sources & evidence

ORD record
ord-c306d61253b94cd991a9eccba5a114fc
Source dataset
uspto-grants-2015_07
Patent number
US09073908B2

Linked notes

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