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

HRID 545473Notes

Reaction equation

HRID 545473 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-d7bddac0f2f54f0c8417565910acffea
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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