Trifluoroacetic acid methylene chloride → 5-Bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid

HRID 29395Notes

Reaction equation

HRID 29395 reaction equation
C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([Br:18])=[C:14]([O:19][CH3:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.ClCCl>>[Br:18][C:15]1[CH:16]=[CH:17][C:10]2[O:9][C:8]([C:6]([OH:7])=[O:5])=[C:12]([CH3:13])[C:11]=2[C:14]=1[O:19][CH3:20]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68714104Tert-butyl 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylate

Product 1

HCID 687165365-Bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acidYield 77%

Procedure

To 220 mg of 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 3 mL of TFA/dichloromethane (1:1) and the solution was stirred at room temperature for 10 h. When the reaction was done, the solvents were removed by vacuum and the residue was triturated with hexane/dichloromethane. Filtration of the suspension gave 141 mg (77% yield) of 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid as a white solid.

Workup

  1. customthe solvents were removed by vacuum
  2. customthe residue was triturated with hexane/dichloromethane
  3. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-13acecdc5268409996dcb77dc0720d71
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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