2-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester → Ethyl 5-hydroxybenzofuran-2-carboxylate

HRID 606580

Reaction equation

HRID 606580 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1

Participants

3

Reactant 1

HCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester

Product 1

HCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 5-methoxybenzofuran carboxylate (22.7 mmol) was dissolved in dichlormethane (20 ml) and a 1.0 M solution of boron tribromide methyl sulphide complex in dichloromethane (68.1 mmol) was added. The mixture was heated at reflux over night The solvent was evaporated under vacuo and the residue purified by flash chromatography to obtain ethyl 5-hydroxybenzofuran carboxylate as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux over night The solvent
  3. customwas evaporated under vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-9919d0ed1faa48e0997bfb8a70d6c37d
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Linked notes

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