4-Toluenesulfonyl chloride → 4-(4-Bromophenoxy)-2-(hydroxymethyl)butyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a suspension of NaH (0.11 g, 4.58 mmol) in anhydrous tetrahydrofuran (10 mL) was added a solution of 2-(2-(4-bromophenoxy)ethyl)propane-1,3-diol (0.63 g, 2.29 mmol) in anhydrous tetrahydrofuran (10 mL) dropwise. The reaction mixture was stirred at room temperature for 30 minutes. Then, tosyl chloride (0.44 g, 2.3 mmol) was added in portions. The reaction mixture was then stirred at room temperature for 2 hours. The reaction mixture was carefully quenched with water and extracted with ethyl acetate (4×30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (0-35% ethyl acetate/petroleum ether) to afford the title compound (0.45 g, 46%) as white solid. 1H NMR (400 MHz, CDCl3) ppm 7.80 (d, 2H), 7.40-7.30 (m, 4H), 6.71 (d, 2H), 4.21-4.09 (m, 2H), 4.00-3.90 (m, 2H), 3.74-3.62 (m, 2H), 2.45 (s, 3H), 2.14 (m, 1H), 1.89-1.74 (m, 3H).

Provenance & Evidence