3,3,3-Trifluoropropionic acid → HCID 67247875, compound

HRID 1027602Notes

Reaction equation

HRID 1027602 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:26]([Cl:29])([F:28])[F:27])([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)[O:15][N:14]=2)=[CH:9][C:8]=1[CH3:30])(C)(C)C.FC(CC(O)=O)(F)F>ClCCl>[Cl:29][C:26]([F:27])([F:28])[C:16]1([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[O:15][N:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:31])=[O:5])=[C:8]([CH3:30])[CH:9]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 27779723,3,3-Trifluoropropionic acidHCID 67247966HCID 67247966, compound

Product 1

HCID 67247875HCID 67247875, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(chloro-difluoro-methyl)-5-(3,5-dichloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid tert-butyl ester (1.95 g) in dichloromethane (20 ml) was added trifluoromethyl acetic acid (“TFA”) (3 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The dichloromethane was removed by distillation. The residue was purified over silica gel (eluent: ethyl acetate/heptane gradient from 1:1 to 1:0) to give 4-[5-(Chloro-difluoro-methyl)-5-(3,5-dichloro-phenyl)-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (1.37 g). 1H-NMR (CDCl3, 400 MHz): 8.10 (d, 1H), 7.65-7.45 (m, 5H), 4.15 (m, 1H), 3.75 (d, 1H), 2.70 (s, 3H).

Workup

  1. customThe dichloromethane was removed by distillation
  2. customThe residue was purified over silica gel (eluent: ethyl acetate/heptane gradient from 1:1 to 1:0)

Sources & evidence

ORD record
ord-31eab90b95924a30a15df7614fe3d3b1
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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