Boron tribromide → 2-Ethyl 6-hydroxybenzo[b]thiophene

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 221436902-Ethyl-6-methoxybenzo[b]thiophene

Product 1

HCID 221435082-Ethyl 6-hydroxybenzo[b]thiopheneYield 82%

Procedure

This material was prepared from 2-ethyl-6-methoxybenzo[b]thiophene 134a (2.30 g, 12 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give a white solid (1.75 g, 82%). 1H NMR (DMSO-d6) δ9.43 (1H, s), 7.48 (1H, d, J=8.5 Hz), 7.16 (1H, d, J=2.2 Hz), 6.95 (1H, s), 6.78 (1H, dd, J=2.2, 8.5 Hz), 2.81 (2H, q, J=7.5 Hz), 1.26 (3H, t, J=7.5 Hz).

Sources & evidence

ORD record: ord-56d31419cf764bab9d8bb60606f8117e
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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