Boron tribromide → 2-ethyl-6-hydroxy-N-methylbenzofuran-3-carboxamide

HRID 985202Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:6]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:7]=2[O:8][C:9]=1[CH2:10][CH3:11])=[O:4].B(Br)(Br)Br>>[CH3:1][NH:2][C:3]([C:5]1[C:6]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:7]=2[O:8][C:9]=1[CH2:10][CH3:11])=[O:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 207677956-Methoxy-2-ethylbenzo[b]furan-3-carboxylic acid methylamide

Product 1

HCID 207677922-ethyl-6-hydroxy-N-methylbenzofuran-3-carboxamideYield 84.3%

Procedure

Example 14(c) was prepared from 6-methoxy-2-ethylbenzo[b]furan-3-carboxylic acid methylamide 14b (401 mg, 1.72 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give 318 mg (84%) of an off-white solid. 1H NMR (DMSO-d6) δ9.53 (1H, s), 7.79 (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), 3.03 (2H, q, J=7.3 Hz), 2.77 (3H, d, J=4.6 Hz), 1.24 (3H, t, J=7.3 Hz). Anal. Calcd for C12H13NO3: C, 65.74; H, 5.98; N, 6.39. Found: C, 65.61; H, 6.06; N, 6.32.

Sources & evidence

ORD record: ord-5301d0ce4a154a30a4034e5da42d37cc
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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