Sodium Hydroxide → 6-Bromo-8-chloro-4,4-dimethylthiochroman

Participants

Reaction Conditions

Reaction Steps

To a mixture of aluminum chloride (0.58 g, 4.34 mmol) and dichloromethane (23.2 mL) cooled to −78° C. was added 4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene (1.15 g, 3.94 mmol) in dichloromethane (6.00 mL) via a cannula to give a light yellow solution. The reaction mixture was allowed to warm to room temperature, stirred for 5 minutes, and then poured into an Erlenmeyer flask containing a cold 10% aqueous NaOH solution (75.0 mL). The mixture was extracted with dichloromethane (2×, 40.0 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil.

Provenance & Evidence