Boron tribromide → 2-Methylbenzofuran-6-ol

HRID 985300Notes

Reaction equation

HRID 985300 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.CNC(C1C2C=CC(O)=CC=2SC=1C)=O>>[OH:2][C:3]1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 130130736-Methoxy-2-methylbenzofuranHCID 207678636-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamide

Product 1

HCID 122034982-Methylbenzofuran-6-olYield 75.5%

Procedure

This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).

Sources & evidence

ORD record
ord-2b3273bbd7e34993a54335a599cf626e
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…