Sodium ethoxide → 5-Bromo-3-methyl-1-benzofuran-2-carboxylic acid

HRID 29296Notes

Reaction equation

HRID 29296 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=O)[CH3:15])C.[O-]CC.[Na+].CO.ClCCl>C(O)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]2[O:6][C:5]([C:4]([OH:3])=[O:17])=[C:14]([CH3:15])[C:8]=2[CH:9]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetateHCID 21226129Dichloromethane methanol

Product 1

HCID 23888285-Bromo-3-methyl-1-benzofuran-2-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (2-acetyl-4-bromo-phenoxy)-acetic acid ethyl ester (2.87 g, 9.5 mmol, 1 eq) and sodium ethoxide (0.65 g, 9.5 mmol, 1 eq) in 100 mL of ethanol under nitrogen was heated to 75° C. for 3 h. After work up followed by column chromatography (20% MeOH/dichloromethane), 5-bromo-3-methyl-benzofuran-2-carboxylic acid was obtained in 72% yield (1.74 g). 1H NMR (400 MHz, CD3OD) δ ppm 2.5 (s, 3 H) 7.5 (d, J=8.8 Hz, 1 H) 7.6 (m, 1 H) 7.9 (d, J=2.0 Hz, 1 H).

Sources & evidence

ORD record
ord-33e25d7ac0304028809c3e0467e63793
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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