Hexane → HCID 67079158, compound

Participants

Reaction Steps

Condition 4: Under a nitrogen atmosphere, 2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene (500 mg, 1.48 mmol) was dissolved in toluene (3.65 ml) and t-butylmethyl ether (0.35 ml). To the solution was added dropwise n-butyllithium in hexane (1.6 M, 1.01 ml, 1.62 mmol) at 0° C. over 30 minutes. After completion of the addition, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a product containing 4-bromide and 2-bromide as an oil (373 mg). According to 1H-NMR analysis of the product, the ratio of 4-bromide:2-bromide was determined as 40:1, which was calculated based on the integration ratio of peaks of protons at benzyl position.

Provenance & Evidence