Trifluoroacetic acid → 5-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

HRID 1172848Notes

Reaction equation

HRID 1172848 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]2[S:9][C:10]([C:12]([O:14]C(C)(C)C)=[O:13])=[CH:11][C:7]=2[CH:6]=1)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]2[S:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59556407Benzo[b]thiophene-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester

Product 1

HCID 595564095-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzo[b]thiophene-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester (3.018 g, 10.32 mmol) and TFA (20 mL) in CH2Cl2 (50 mL) was allowed to stir at rt for four days. The reaction mixture was concentrated and dried under high vacuum to give benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester as a pale solid. MS (EI): cal'd 237.0 (MH+), exp 237.1 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-3f805adbaac54592967313b717127e28
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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