4-Bromophenol → HCID 69144624, compound

Participants

Reaction Steps

To a mixture of Example 69A (˜53.05 mmol) and 4-bromophenol (13.80 g, 79.76 mmol) in DMSO (50 mL) cooled with an ice-bath was added NaH (60%, 3.20 g, 80.0 mmol) in several portions. After the addition, the mixture was stirred at room temperature for 10 minutes. To this was added 18-crown-6 (16.0 mL, 80.6 mmol). The reaction mixture was heated to 160° C. for 60 hours. The mixture was poured into 1N NaOH, extracted with ethyl acetate (2×). The combined extracts were washed with water (1×), brine (1×), dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate and hexane to give the desired product as yellow oil (11.1 g).

Provenance & Evidence