Trifluoroacetic acid → 5-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid

HRID 1849596Notes

Reaction equation

HRID 1849596 reaction equation
[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([C:26]([F:29])([F:28])[F:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([O:11]C(C)(C)C)=[O:10])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[C:5]([O:18][CH2:19][C:20]3([C:26]([F:29])([F:27])[F:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[CH:6][C:7]([F:17])=[C:8]([CH:16]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86703449Tert-butyl 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)cyclohexyl)methoxy)benzoate

Product 1

HCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)-methoxy)benzoate (3.70 g, 8.88 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (10 ml). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated in vacuo. The residue was triturated in hexanes (10 mL), the solid was filtered and dried to give the title compound (2.20 g, 69%): 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=8.1 Hz, 1H), 6.59 (d, J=12.3 Hz, 1H), 4.11 (s, 2H), 2.03-1.88 (m, 3H), 1.76-1.60 (m, 5H), 1.50-1.21 (m, 3H), 0.94-0.83 (m, 2H), 0.64-0.55 (m, 2H); MS (ES+) m/z 361.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated in hexanes (10 mL)
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-62de438a694949a5a7b7a6bb7a3f6aab
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…