Boron tribromide → 6-Hydroxy-2-(1-methylethyl)benzofuran-3-carboxylic acid methylamide

HRID 985205Notes

Reaction equation

HRID 985205 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][C:7]=2[O:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4].B(Br)(Br)Br>>[CH3:1][NH:2][C:3]([C:5]1[C:6]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:7]=2[O:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 207678016-Methoxy-N-methyl-2-(1-methylethyl)-3-benzofurancarboxamide

Product 1

HCID 207678606-Hydroxy-2-(1-methylethyl)benzofuran-3-carboxylic acid methylamide

Procedure

This material was prepared from 6-methoxy-2-(1-methylethyl)benzo[b]furan-3-carboxylic acid methylamide 15b (173 mg, 0.84 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give 157 mg (80%) of a crisp foam. 1H NMR (DMSO-d6) δ9.54 (1H, s), 7.76 (1H, d, J=4.6 Hz), 7.45 (1H, d, J=8.6 Hz), 6.88 (1H, d, J=2.0 Hz), 6.74 (1H, dd, J=2.0, 8.6 Hz), 3.68-3.61 (1H, m), 2.75 (3H, d, J=4.6 Hz), 1.24 (6H, d, J=7.1 Hz).

Workup

  1. customto give 157 mg (80%) of a crisp foam

Sources & evidence

ORD record
ord-1e8e90d7a3714c379b45b6bd4d3b27a1
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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