Triphenylphosphine → 2-(2-Bromoethyl)cyclopropylmethyl t-butyldimethyl silyl ether

Participants

Reaction Conditions

Reaction Steps

2-(2-hydroxyethyl)cyclopropylmethyl t-butyldimethylsilyl ether (15.0 g, 65 mmol) was dissolved in N,N-dimethylformamide (120 ml), and triphenylphosphine (17.3 g, 66 mmol) was added thereto at room temperature. Twenty minutes later, the mixture was cooled to -20° C. Bromine (10.5 g, 66 mmol) was added thereto over a period of 5 minutes, and the temperature was gradually raised to 0° C. The mixture was poured into a saturated sodium hydrogen carbonate aqueous solution, and the product was extracted with ethyl ether. Then, it was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain 2-(2-bromoethyl)cyclopropylmethyl t-butyldimethylsilyl ether (2.7 g).

Provenance & Evidence