Trifluoroacetic acid → HCID 89580473, compound

HRID 1479742Notes

Reaction equation

HRID 1479742 reaction equation
[CH:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10]C(C)(C)C)=[O:9])=[CH:6][C:5]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89580871HCID 89580871, compound

Product 1

HCID 89580473HCID 89580473, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-isopropyl-3-phenoxybenzoate (150 mg, 0.48 mmol) in dichloromethane (10 mL) was added 2,2,2-trifluoroacetic acid (2 mL). The resultant mixture was stirred at room temperature for 30 minutes. Thin layer chromatography showed that starting material was consumed completely. The solution was concentrated to give 4-isopropyl-3-phenoxybenzoic acid (100 mg, 81.3%) as a white solid which was used in the next step directly. LRMS (M+H+) m/z: calcd 257.11. found 257. 1H NMR (300 MHz, DMSO) δ 12.94 (s, 1H), 7.71 (m, 1H), 7.68 (m, 1H), 7.40 (m, 2H), 7.38 (s, 1H), 7.36 (m, 1H), 7.11 (m, 2H), 1.22 (s, 6H).

Workup

  1. customwas consumed completely
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-acff23cda6034a95a87f1d635765c4d0
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

Loading…