1-bromoethenylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: ##STR20## A solution of 5 g (25 mmol) of α-bromostyrene in 10 ml of absolute diethyl ether is added dropwise to a mixture of 0.7 g (30 mmol) of magnesium filings and 10 ml of diethyl ether under an argon atmosphere and with stirring at room temperature. After the addition has ended, the reaction mixture is refluxed for 1 hour. The resulting Grignard solution is added dropwise at room temperature with stirring to a solution of 3 g (20 mmol) of 1-chlorocyclopropyl chloromethyl ketone in 10 ml of diethyl ether. After the addition has ended, the mixture is refluxed for another 4 hours. The reaction mixture is subsequently treated with a saturated, aqueous ammonium chloride solution, the resulting mixture is poured into water, and this mixture is extracted repeatedly using diethyl ether. The combined organic phase are washed with saturated, aqueous sodium chloride solution, dried over sodium sulphate, and then concentrated by stripping off the solvent under reduced pressure. 5.0 g (97% of theory) of 1-chloro-2-(1-chlorocyclopropyl)-3-phenyl-but-3-en-2-ol are obtained. After the addition the reaction mixture is refluxed for 1 hour The resulting Grignard solution is added dropwise at room temperature After the addition the mixture is refluxed for another 4 hours this mixture is extracted repeatedly using diethyl ether The combined organic phase are washed with saturated, aqueous sodium chloride solution dried over sodium sulphate concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of α-bromo styrene (5.5 g, 30 mmol) in diethyl ether (30 mL) at −78° C. was treated with a solution of tert-BuLi (1.7 M solution, 21.2 mL, 36 mmol), stirred at −78° C. for 0.5 hours, treated with triisopropyl borate (8.31 mL, 36 mmol) over 48 minutes, stirred for 1 hour, warmed to room temperature over 18 hours, diluted with diethyl ether (100 mL), treated with 1M HCl (100 mL), stirred at room temperature for 5 hours, concentrated to remove the THF, adjusted pH 14 with IN NaOH, washed with hexane, adjusted to pH 1 with 1M HCl, and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered and concentrated to provide the title compound. stirred for 1 hour warmed to room temperature over 18 hours stirred at room temperature for 5 hours concentrated to remove the THF, adjusted pH 14 with IN NaOH washed with hexane extracted with ethyl acetate The extract was dried (Na2SO4) filtered concentrated