Trifluoroacetic acid methylene chloride → 4-Isopropoxy-3-methyl-benzofuran-2-carboxylic acid

HRID 29353Notes

Reaction equation

HRID 29353 reaction equation
C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.ClCCl>>[CH:19]([O:18][C:14]1[C:11]2[C:12]([CH3:13])=[C:8]([C:6]([OH:7])=[O:5])[O:9][C:10]=2[CH:17]=[CH:16][CH:15]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 687150563-Methyl-4-isopropoxy-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687160934-Isopropoxy-3-methyl-benzofuran-2-carboxylic acidYield 118.3%

Procedure

To 220 mg of 4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 3 mL of TFA/dichloromethane (1:1). The solution was stirred at room temperature for 3 h. The solvents were removed under vacuum and the residue was triturated with acetonitrile. Filtration of the precipitate gave 210 mg of 4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid as a white solid.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was triturated with acetonitrile
  3. filtrationFiltration of the precipitate

Sources & evidence

ORD record
ord-ff7bf0478ef546108897b086118c5250
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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