2-(4-bromo-2-ethoxyphenyl)ethanol

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

Procedure: NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+. the cooling bath was removed was added the mixture was extracted with diethyl ether The combined organics were washed with brine dried over Na2SO4 concentrated in vacuo The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

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

Procedure: NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+. the cooling bath was removed was added the mixture was extracted with diethyl ether The combined organics were washed with brine dried over Na2SO4 concentrated in vacuo The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

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

Procedure: Using a procedure analogous to that used to prepare 30B, 62D (700 mg, 3.3 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 62E (620 mg, 82%) as solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (t, J=6.95 Hz, 3 H) 2.85 (t, J=6.32 Hz, 2 H) 3.81 (t, J=6.32 Hz, 2 H) 4.02 (q, J=7.07 Hz, 2 H) 6.96 (s, 1 H) 6.99-7.03 (m, 2 H).

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

Procedure: NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+. the cooling bath was removed was added the mixture was extracted with diethyl ether The combined organics were washed with brine dried over Na2SO4 concentrated in vacuo The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

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

Procedure: Using a procedure analogous to that used to prepare 30B, 62D (700 mg, 3.3 mmol) was heated in a pressure vessel with 9-BBN at 100° C. for 10 h and worked up as in 30B to yield 62E (620 mg, 82%) as solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (t, J=6.95 Hz, 3 H) 2.85 (t, J=6.32 Hz, 2 H) 3.81 (t, J=6.32 Hz, 2 H) 4.02 (q, J=7.07 Hz, 2 H) 6.96 (s, 1 H) 6.99-7.03 (m, 2 H).