Trifluoroacetic acid → 2-Chloro-4-isopropylbenzoic acid

HRID 1479720Notes

Reaction equation

HRID 1479720 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89580719HCID 89580719, compound

Product 1

HCID 198202302-Chloro-4-isopropylbenzoic acidYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of tert-butyl 2-chloro-4-isopropylbenzoate (150 mg, 0.59 mmol) in dichloromethane (10 mL) was added 2,2,2-trifluoroacetic acid (2 mL) at room temperature. The resultant reaction mixture was stirred at 30° C. for 30 minutes. Thin layer chromatography showed that starting material was consumed completely. The solution was concentrated under reduced pressure to give 2-chloro-4-isopropylbenzoic acid (100 mg, 85.5%) as a white solid which was used in the next step directly. LRMS (M+H+) m/z: calcd 199.04. found 199.

Workup

  1. customThe resultant reaction mixture
  2. customwas consumed completely
  3. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-98930fd4a26e468f9b32b1e5a6be974b
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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