Water → 4-Bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

HRID 9881Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[S:5][C:6]=1Br.C([Li])CCC.CCCCCC.O>O1CCCC1>[Br:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[S:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

4,5-Dibromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (13.88 g (33.6 mmol), prepared as described in 4)) was dissolved in tetrahydrofuran (140 ml). To the solution was added dropwise at −78° C. a solution of 1.59 M butyl lithium/hexane (23.3 ml, 37 mmol). The resulting mixture was stirred at −78° C. for 15 minutes. At the end of this time, water (24 ml) was added to the reaction mixture and it was allowed to warm to room temperature. The reaction mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue (solid) was washed with diethyl ether, to give the title compound (11.20 g) as a pale brown powder (yield quantitative).

Workup

temperatureto warm to room temperature
customThe reaction mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed by distillation under reduced pressure
washThe residue (solid) was washed with diethyl ether

Sources & evidence

ORD record: ord-b04067277869419fae990d7fe5bba5e8
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091352B2

Reaction notes

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