Tetrahydrofuran → Methyl 3-[(methylsulfonyl)oxy]-4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

In a 1 liter round-bottomed flask were placed methyl 3-hydroxy-4-nitrobenzoate (21.7 g, 0.11 mole) and tetrahydrofuran (400 ml). To the resulting well-stirred mixture was added triethylamine (13.3 g, 0.132 mole) dropwise at -20° C. The reaction mixture was stirred at -20° C. for 10 minutes. Methanesulfonyl chloride (13.9 g, 0.121 mole) in methylene chloride (approximately 10 ml) was added slowly dropwise at such a rate as to keep the temperature at -20° C. After the addition was complete the reaction mixture was warmed up slowly to 0° C. and stirred at that temperature for 1 hour. The reaction mixture was poured into a mixture of water (500 ml) and ethyl ether (300 ml). The aqueous layer was separated and extracted with ethyl ether (2×300 ml). The combined ether layers were washed with water (2×250 ml), brine (1×250 ml) and dried over magnesium sulfate. The solvent was removed in the rotary evaporator and the resulting crude product triturated with hexane yielding 22.8 g of the expected methyl 3-methylsulfonyloxy-4-nitrobenzoate which was used as such in the next step.

Provenance & Evidence