p-Fluoronitrobenzene → HCID 11077303, compound

Participants

Reaction Steps

To a suspension of sodium hydride (2.48 g, 98.1 mmol) (Aldrich, 95%) in tetrahydrofuran (150 mL) was added a solution of 3-(Boc-amino)-1-propanol (8.1 g, 46.8 mmol) (Aldrich) in tetrahydrofuran (25 mL) at −10° C. After stirred for 15 minutes, the reaction was allowed to warm to room temperature and stirred for a further 30 minute. To this mixture was added a solution of 1-fluoro-4-nitro-benzene (6.92 g, 49.07 mmol) (Aldrich) and the reaction was stirred at room temperature for 2 hours. The resulting mixture was poured in cool aqueous ammonium chloride solution (100 mL). The aqueous layer was extracted with ethyl acetate (3×40 mL) and the combined organic extracts were washed with brine (3×30 mL), dried (Na2SO4) and evaporated in vacuo. The residue was purified on silica gel with 85:15 hexane/ethyl acetate to provide [3-(4-nitrophenoxy)propyl]carbamic acid tert-butyl ester (10.6 g, 73% yield) as light yellow solid. MS (ES) MH+=297.

Provenance & Evidence