2-氟-3-羟基苯腈

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred solution of 2-fluoro-3-hydroxybenzonitrile (800 mg, 5.83 mmol) in DMF (10 mL) at 0° C. was treated portionwise with NaH (280 mg, 7.00 mmol) (60% oil dispersion). The reaction mixture was then stirred for 0.5 h and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1490 mg, 6.42 mmol) was added. The reaction was allowed to warm to rt overnight with stirring. The reaction mixture was then treated with water (40 mL) and brine (5 mL) and extracted with ethyl acetate (˜50 mL). The organic extract was washed with water, dried over anhydrous Na2SO4, filtered and conc. in vacuo to afford a residue which was purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes) to yield the title compound as a white solid (1040 mg, 81%). 1H NMR (400 MHz, MeOD) δ ppm 7.56 (td, 1 H), 7.47-7.38 (m, 1 H), 7.38-7.24 (m, 1 H), 4.73 (q, 2 H); m/z 220. with stirring extracted with ethyl acetate (˜50 mL) The organic extract was washed with water dried over anhydrous Na2SO4 filtered and conc. in vacuo to afford a residue which was purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes)

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 100 mL round bottom flask was charged with a magnetic stir bar, 2-fluoro-3-hydroxybenzonitrile (0.500 g, 3.65 mmol), MeCN (13.89 ml), 1-bromo-2-methylpropane (0.699 ml, 7.29 mmol), and K2CO3 (1.008 g, 7.29 mmol). The mixture was then placed in an oil bath and heated to 60° C. with stirring overnight. This mixture was then cooled to rt, filtered through a bed of Celite, and conc. In vacuo. The crude material was purified via silica gel chromatography (40 g) using ethyl acetate/hexanes (1:4) as eluent to afford pure 2-fluoro-3-isobutoxybenzonitrile (0.610 g, 87%) as a colorless oil. M/z 194. A 100 mL round bottom flask was charged with a magnetic stir bar The mixture was then placed in an oil bath This mixture was then cooled to rt filtered through a bed of Celite The crude material was purified via silica gel chromatography (40 g)