5-Hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole → 3-(4-Chlorophenyl)-5-(trifluoromethyl)isoxazole

HRID 2262573Notes

Reaction equation

HRID 2262573 reaction equation
[Cl: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>>[Cl: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 28811613-(4-Chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol

Product 1

HCID 7993213-(4-Chlorophenyl)-5-(trifluoromethyl)isoxazoleYield 98%

Procedure

As described for Example 1b, 3-(4-chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-ol (39.6 g, 149 mmol), instead of 3-phenyl-5-hydroxy-5-(trifluoromethyl)isoxazoline, was converted to the title compound (36.0 g, 98%) which was obtained as a light brown oil. MS: m/e=247.3 [M−H]−.

Sources & evidence

ORD record
ord-c837689e58f8465fb3ea26fde94cd2c7
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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