Boron tribromide → HCID 17981923, compound

Reaction equation

B(Br)(Br)Br.[F:5][C:6]1[C:14]2[CH2:13][CH2:12][S:11][C:10]=2[C:9]([O:15]C)=[CH:8][CH:7]=1.OC1C2N=CSC=2C=CC=1>>[F:5][C:6]1[C:14]2[CH2:13][CH2:12][S:11][C:10]=2[C:9]([OH:15])=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 25134Boron tribromide

HCID 819014-Hydroxybenzothiazole

HCID 179819214-Fluoro-7-methoxy-2,3-dihydrobenzo[b]thiophene

Product 1

HCID 17981923HCID 17981923, compound

Procedure

A BBr3 demethylation of 4-fluoro-7-methoxy-2,3-dihydrobenzo[b]thiophene similar to that described for 4-hydroxy benzothiazole affords the title compound as a brown solid 251 Mg: δH (300 MHz, CDCl3) 6.57-6.48 (2H, m, ArH), 4.67 (1H, br. s, OH) and 3.43-3.23 (4H, m, SCH2CH2).

Sources & evidence

ORD record: ord-8405399ed8cc4636bb8e96b89e52c3ef
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417064B2

Reaction notes

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