Trifluoroacetic acid methylene chloride → 3-Methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid

HRID 29361Notes

Reaction equation

HRID 29361 reaction equation
C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[C:11]=2[C:12]=1[CH3:13])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.ClCCl>>[CH3:13][C:12]1[C:11]2[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[CH:15][CH:16]=[CH:17][C:10]=2[O:9][C:8]=1[C:6]([OH:7])=[O:5]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 687152023-Methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687100553-Methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acidYield 92%

Procedure

To 300 mg of 3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid tert-butyl ester was added 4 mL of TFA/dichloromethane (1:1). The solution was stirred at room temperature for 5 h. The solvents were removed under vacuum and the residue was triturated with ether. Filtration gave 232 mg (92% yield) of 3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid as white solid.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was triturated with ether
  3. filtrationFiltration

Sources & evidence

ORD record
ord-ab6c9ca0d7e3448f9d3dc917bab48680
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…