Boron tribromide → 2-Methyl-1-benzothiophen-6-OL

HRID 985194Notes

Reaction equation

HRID 985194 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 221434866-Methoxy-2-methylbenzo[b]thiophene

Product 1

HCID 122034952-Methyl-1-benzothiophen-6-OLYield 93.2%

Procedure

This material was prepared from 6-methoxy-2-methylbenzo[b]thiophene 1b (2.92 g, 16.4 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give 2.51 g (93%) of a white solid. 1H NMR (DMSO-d6) δ9.43 (1H, s), 7.47 (1H, d, J=8.5 Hz), 7.14 (1H, d, J=2.2 Hz), 6.92 (1H, s), 6.78 (1H, dd, J=2.2, 8.5 Hz), 2.46 (3H, s). Anal. Calcd. for C9H8OS: C, 65.82; H, 4.91; S, 19.53. Found: C, 65.96; H, 5.11; S, 19.69.

Sources & evidence

ORD record
ord-14ab80e70d8548c38b65c6c81a6b2b5f
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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