1-(2-溴苯基)丙-2-烯-1-醇

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

实验步骤: To 1-(2-bromophenyl)prop-2-en-1-ol) (31.0 g; 0.145 mol) in 150 ml of dry THF (tetrahydrofuran) was added 20 ml of 3,4-dihydro-2H-pyran and then 1 ml of POCl3 and the mixture stirred over the weekend at room temperature. The reaction mixture was neutralized with saturated NaHCO3 and concentrated down. The resulting material was partitioned between water and diethyl ether and the aqueous layer extracted again with diethyl ether. The organics were combined and washed with water and then brine and dried over K2CO3 and concentrated. The crude subtitle compound was chromatographed by HPLC using a solvent gradient from pure hexane to 5% ethyl acetate in hexane to afford the subtitle compound. concentrated down The resulting material was partitioned between water and diethyl ether the aqueous layer extracted again with diethyl ether washed with water brine and dried over K2CO3 concentrated The crude subtitle compound was chromatographed by HPLC

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

实验步骤: To 2-bromobenzaldehyde (27 g; 0.146 mmol.) in dry tetrahydrofuran cooled to -78° C. in a dry ice/isopropyl alcohol bath was added 175 ml of a 1.0M solution of vinyl Grignard reagent in tetrahydrofuran dropwise and the reaction allowed to slowly warm overnight to room temperature. The reaction mixture was quenched with saturated NH4Cl and the tetrahydrofuran was concentrated off. The reaction mixture was poured into water and extracted twice with diethylether, washed with water and then brine and dried over K2CO3 to afford the subtitle compound. The reaction mixture was quenched with saturated NH4Cl the tetrahydrofuran was concentrated off The reaction mixture was poured into water extracted twice with diethylether washed with water brine and dried over K2CO3

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

实验步骤: To a suspension of NaH (1.23 g, 28.2 mmol, 1.2 equiv., 60% content) in THF (10 mL) was added a solution of 1-(2-bromophenyl)prop-2-en-1-ol (5.0 g, 23.5 mmol, 1.0 eq) in THF (10 mL) dropwise at 0° C. The mixture was stirred for 1 h, then, cooled to −70° C. n-BuLi (11.3 mL, 28.2 mmol, 1.2 eq., 2.5M in THF) was added. The mixture was stirred for 1 h, then, triisopropyl borate (5.3 g, 28.2 mmol, 1.2 equiv.) was added. The mixture was stirred for 5 h, then, quenched with 2N H2SO4. The mixture was partitioned between brine and ethylacetate. The organic layer was washed over brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to yield 3-vinylbenzo[c][1,2]oxaborol-1(3H)-ol (2.2 g, 57%). LC-MS (m/z)=158.9, 160.9 [M+H]+. was added The mixture was stirred for 1 h The mixture was stirred for 5 h quenched with 2N H2SO4 The mixture was partitioned between brine and ethylacetate The organic layer was washed over brine dried over Na2SO4 filtered concentrated The residue was purified by column chromatography

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

实验步骤: To a solution of allylmagnesium bromide (108 mL, 108 mmol, 2.0 eq) in THF was added a solution of 2-bromobenzaldehyde (10 g, 54 mmol, 1.0 eq) in THF (20 mL) dropwise at −18° C. The mixture was allowed to reach room temperature for 17 h, then, quenched with saturated NH4Cl aqueous. The mixture was partitioned between brine and ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to provide 1-(2-bromophenyl)prop-2-en-1-ol (10.5 g, 91%). LC-MS (m/z)=213.0 [M+H]+. quenched with saturated NH4Cl aqueous The mixture was partitioned between brine and ethyl acetate The organic layer was washed with brine dried over Na2SO4 filtered concentrated The residue was purified by column chromatography