(4-氯-3-碘苯基)甲醇

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Triphenylphosphine (1.1 g) was added in portions to a solution of 4-chloro-3-iodobenzyl alcohol (1.1 g) in dichloromethane (40 ml) at 0° C. and stirring was continued for 10 minutes. Carbon tetrabromide (1.5 g) was then added in portions over 2 minutes, the reaction mixture was allowed to warm to ambient temperature and was stirred for 15 hours. The solution was added directly to a silica charged chromatography column and was eluted with dichloromethane to give 4-chloro-3-iodobenzyl bromide (1.9 g). NMR (CD3SOCD3): d 4.6 (s, 2H), 7.5 (m, 2H), 7.6 (s, 1H), 8.0 (m, 1H). was stirred for 15 hours The solution was added directly to a silica charged chromatography column was eluted with dichloromethane

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

实验步骤: Borane-THF complex (10 ml) was added dropwise over 20 minutes to a solution of 4-chloro-3-iodobenzoic acid (1.4 g) in THF (25 ml). The reaction mixture was stirred for 2 hours and then cooled (ice bath) and methanol (20 ml) was added cautiously. The solvent was removed and the residue was dissolved in methanol (10 ml) and stirred with aq. 2M sodium hydroxide (10 ml) for 2 hours. Ethyl acetate (50 ml) was added and the mixture was washed with saturated aq. sodium bicarbonate solution (50 ml). The aqueous extracts were washed with ethyl acetate (2×50 ml) and the combined ethyl acetate extracts were washed with water (50 ml) and brine (50 ml) and died. Removal of the solvent gave 4-chloro-3-iodobenzyl alcohol (1.15 g). NMR (CD3SOCD3): d 4.45 (d, 2H), 5.3 (t, 1H), 7.3 (m, 1H), 7.5 (m, 1H), 7.8 (s, 1H). was added cautiously The solvent was removed the residue was dissolved in methanol (10 ml) stirred with aq. 2M sodium hydroxide (10 ml) for 2 hours Ethyl acetate (50 ml) was added the mixture was washed with saturated aq. sodium bicarbonate solution (50 ml) The aqueous extracts were washed with ethyl acetate (2×50 ml) the combined ethyl acetate extracts were washed with water (50 ml) and brine (50 ml) Removal of the solvent