Monobenzone → HCID 2799699, compound

Participants

Reaction Steps

A solution of 4-benzyloxyphenol (6.01 g, 30 mmol) in anhydrous dimethylformamide (50 ml) under a nitrogen cover was treated with sodium hydride (1.2 g of 60% oil dispersion, 30 mmol) in one portion at room temperature. A moderate gas evolution ensued, and the reaction temperature rose to 41° C. After stirring an additional 35 minutes, 4-Fluoronitrobenzene was added rapidly dropwise, neat via syringe. A mild exotherm brought the reaction temperature to 32° C., after which the reaction was stirred for 18 hours at room temperature. The reaction mixture was poured over ice/water (250 ml), stirred for thirty minutes and the yellow solid collected by suction filtration. Silica gel chromatography (Waters® LC2000; two Pre-Pak® columns, P eluting with 3/1 hexanes/methylene chloride) afforded 4-(4-benzyloxyphenoxy)-1-nitrobenzene (5.9 g, 73%) as a white solid. 1H NMR(400 MHZ): 5.08(2H,s), 6.94-6.99(2H,m), 7.02(4H,s), 7.32-7.47(5H,m), 8.15-8.20(2H,m); MS(ESI)m/z 320.2([M−H]−,100).

Provenance & Evidence