2-bromo-4-(2-hydroxyethyl)benzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: LiBH4 (1.48 mL, 2.95 mmol, 2 M in THF) was added to a stirred solution of methyl(3-bromo-4-cyanophenyl)acetate (0.50 g, 2.0 mmol) in THF (25 ml) at 0° C. The resulting solution was stirred for 12 h. Water (15 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure to yield the crude product as a cloudy oil. 1H NMR (500 MHz, CDCl3) δ 7.63 (s, 1H), 7.61 (d, J=5.7, 1H), 7.33 (d, J=7.8 Hz, 1H), 3.93 (t, J=1.6, J=4.8 Hz, 2H), 2.92 (t, J=6.6, J=5.1 Hz, 2H). LC-MS (IE, m/z): 210.1 [(M+1)]+−OH]. the resulting solution was extracted with dichloromethane (2×50 ml) The combined organic layers were dried over MgSO4 filtered evaporated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-Bromo-4-(2-hydroxyethyl)benzonitrile (220 mg, 1.0 mmol) in DCM (15 mL) was added Dess-Martin reagent (1.2 g, 2.8 mmol) and the mixture was stirred at RT for 4 hours. The mixture was washed with water, dried over Na2SO4, and concentrated in vacuo to give the title product. 1H NMR (400 MHz, CDCl3) δ 9.77 (t, J=1.6 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.55 (d, J=1.6 Hz, 1H), 7.25 (dd, J=7.8, 1.6 Hz, 1H), 3.78 (d, J=1.6 Hz, 2H). The mixture was washed with water dried over Na2SO4 concentrated in vacuo