Bromoacetic Acid → 4-Bromo-2-ethyl-1-methanesulfonyl-benzene

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium sulfite (4.44 g, 35.3 mmol) and sodium bicarbonate (2.96 g, 35.3 mmol) in water (100 mL) at 70° C. was added 4-bromo-2-ethyl-benzenesulfonyl chloride (5 g, 17.6 mmol) in dioxane (20 mL) drop-wise via an addition funnel. After an hour, the mixture was heated at 100° C. and bromoacetic acid (4.90 mL, 35.3 mmol) was added. After an hour, the reaction mixture was cooled to 90° C., and sodium hydroxide (2.82 g, 70.5 mmol) was added. The resulting mixture was stirred at 90° C. overnight. After cooling to room temperature, water was added to the resulting suspension. The aqueous layer was extracted with dichloromethane (250 mL×3). The collected organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give 4-bromo-2-ethyl-1-methanesulfonyl-benzene (4.62 g, 100%), which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 7.89 (d, J=8.5 Hz, 1 H), 7.56 (d, J=1.5 Hz, 1 H), 7.51 (dd, J=8.5, 1.5 Hz, 1 H), 3.07 (s, 3 H), 3.05 (q, J=7.4 Hz, 2 H), 1.33 (t, J=7.4 Hz, 3 H).

Provenance & Evidence