1-Bromo-3-chloropropane → HCID 21181453, compound

Participants

Reaction Steps

To a solution consisting of a 0.5 M solution of bis(trimethylsilyl)amide in toluene (2.2 mL, (1.1 mmoles) and tetrahydrofuran (7.8 mL) stirring at −78° under an argon atmosphere was added dropwise a solution of the compound of Example 7, Step (a) (227 g, 1.00 mmole) in tetrahydrofuran (1.0 mL). After stirring for 1.0 hour at −78°, 3-bromo-1-chloropropane (236 mg, 1.50 mmoles) was added in one portion, and the resulting mixture was stirred for 30 minutes at −78° and then 2.0 hours at room temperature. The mixture was partitioned between diethyl ether and water, the aqueous layer was extracted with ether, and the combined organic extracts were washed with water and then brine. After drying over sodium sulfate, the solution was filtered and then evaporated. A compound (271 mg) was obtained as a red oil which was characterized by NMR as follows: 1H NMR(CDCl3) d 7.65(d, 2H), 7.53(d, 2H), 3.48(m, 2H), 1.19(d, 3H), 0.79(d, 3H).

Provenance & Evidence