1,3-Dibromopropane → HCID 54222889, compound

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Reaction Steps

To a stirred, chilled (-65° C.) solution of 2-[2-(benzo[b]thiophen-2-yl)-ethenyl]thiophene (8.1 g) and tetrahydrofuran (100 ml) was added over 15 mins phenyl lithium (18 ml of a 2.0M solution in cyclohexane). The mixture was stirred for 1 hr, and 1,3-dibromopropane (40.5 g) was added. The solution was allowed to warm to room temperature, and was refluxed overnight. The reaction mixture was quenched with methanol (30 ml) and water (100 ml). The organic phase was evaporated in vacuo, and the residue was extracted with dichloromethane. The combined, dried over anhydrous sodium sulfate organic phase was concentrated. The residue was purified by high pressure liquid chromatography (silica gel, eluted with 7:1 hexane: dichloromethane). The appropriate fractions were combined and evaporated to yield 2.15 g (18%) of product, mp 109°-111° C.

Provenance & Evidence