2-iodo-3-methoxybenzyl alcohol

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

Procedure: To a solution of (2-iodo-3-methoxyphenyl)methanol (0.350 g, 1.33 mmol), (Organic Letters, 2001, vol. 3, #21 p. 3245-3248) imidazole (0.181 g, 2.65 mmol) and triphenyl phosphine (0.382 g, 1.46 mmol) in tetrahydrofuran (5 mL) at 0° C. was added Diethyl azodicarboxylate (40% solution in toluene; 0.664 mL). The yellow solution was allowed to warm to room temperature and stirred at 60° C. overnight. After evaporating the solvent under reduced pressure, the crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes). Yield=43%. 1H NMR: 3.90 (s, 3H), 5.19 (s, 2H), 6.43 (d, 1H, J=5.70 Hz), 6.77 (d, 1H, J=6.09 Hz), 6.93 (s, 1H), 7.10 (s, 1H), 7.24 (t, 1H, J=6.03 Hz) After evaporating the solvent under reduced pressure the crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes)

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

Procedure: To a solution of (2-iodo-3-methoxyphenyl)methanol (0.350 g, 1.33 mmol), (Organic Letters, 2001, vol. 3, #21 p. 3245-3248) imidazole (0.181 g, 2.65 mmol) and triphenyl phosphine (0.382 g, 1.46 mmol) in tetrahydrofuran (5 mL) at 0° C. was added Diethyl azodicarboxylate (40% solution in toluene; 0.664 mL). The yellow solution was allowed to warm to room temperature and stirred at 60° C. overnight. After evaporating the solvent under reduced pressure, the crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes). Yield=43%. 1H NMR: 3.90 (s, 3H), 5.19 (s, 2H), 6.43 (d, 1H, J=5.70 Hz), 6.77 (d, 1H, J=6.09 Hz), 6.93 (s, 1H), 7.10 (s, 1H), 7.24 (t, 1H, J=6.03 Hz) After evaporating the solvent under reduced pressure the crude was purified by column chromatography (5% EtOAc:hexanes, 20% EtOAc; Hexanes)