1,4-Dibromobutane → 6-(4-Bromo-butoxy)-3-(4-bromo-phenyl)-benzo[b]thiophene

HRID 347161Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][O:17][C:14]1[CH:15]=[CH:16][C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:12][S:11][C:10]=2[CH:13]=1

Participants

Conditions

Temperature: 45 °C

Procedure

2.0 g (6.55 mmol) 3-(4-Bromo-phenyl)-benzo[b]thiophen-6-ol in 25 ml acetone were treated with 5.89 g (42.6 mmol, 6.5 eq) K2CO3 and 2.0 ml (16.38 mmol, 2.5 eq) 1,4-dibromobutane. The reaction mixture was stirred at 45° C. for 10 h, filtered and evaporated. The excess of dibromide was removed in vacuo to yield 2.7 g crude 6-(4-Bromo-butoxy)-3-(4-bromo-phenyl)-benzo[b]thiophene, MS: 439 (M).

Workup

filtrationfiltered
customevaporated
customThe excess of dibromide was removed in vacuo

Sources & evidence

ORD record: ord-48f1c044e12949d1aa7a1f6852fc9a3a
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173043B2

Reaction notes

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