Trifluoroacetic acid → 2-Chloro-5-(1-methylethyl)benzeneacetic acid

HRID 1854583Notes

Reaction equation

HRID 1854583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117720579Tert-butyl 2-(2-chloro-5-isopropyl-phenyl)acetate

Product 1

HCID 235305592-Chloro-5-(1-methylethyl)benzeneacetic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tert-butyl 2-(2-chloro-5-isopropyl-phenyl)acetate (483 mg, 1.80 mmol) in dichloromethane (5.1 mL). Add trifluoroacetic acid (1.09 mL, 14.4 mmol) slowly and stir the reaction mixture 3 hours at ambient temperature. Concentrate under reduced pressure to give the title compound (380 mg, 1.79 mmol). MS (m/z): 229.8 (M+18). The following compound is prepared essentially by the method of Preparation 49.

Workup

  1. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-6afe9967bbf54ca2931756e74d37d411
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

Loading…