1-(2-bromoethyl)-3-methoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The solution of 1-(2-bromoethyl)-3-methoxybenzene (10 g, 46.4 mmol), NaCN (2.73 g, 55.8 mmol) in dry DMF (20 ml) was heated at 90° C. for 6 hours or until all the starting material is consumed, the reaction was cooled, diluted with EtOAc (60 ml) and washed with water (20 ml×3), brine, the organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound as an oil. is consumed the reaction was cooled diluted with EtOAc (60 ml) washed with water (20 ml×3), brine the organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of benzaldehyde (920 μl, 9 mmol) in dry THF (20 mL) was added slowly a solution of 2-(3-methoxyphenyl) ethylmagnesium bromide prepared from 2-(3-methoxyphenyl) ethyl bromide (2.1 g. 9.77 mmol) and magnesium (300 mg, 12 mmol). The mixture was stirred at room temperature for ½ hour then quenched with saturated NH4Cl. The mixture was then extracted into EtOAc, washed with H2O, dried (Na2SO4), filtered and concentrated in vacuo, then purified by silica gel chromatography (30% EtOAc/Hexane) to provide the desired product as a colorless viscous oil. then quenched with saturated NH4Cl The mixture was then extracted into EtOAc washed with H2O dried (Na2SO4) filtered concentrated in vacuo purified by silica gel chromatography (30% EtOAc/Hexane)

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

Procedure: To a solution of benzaldehyde (920 μl, 9 mmol) in dry THF (20 mL) was added slowly a solution of 2-(3-methoxyphenyl) ethylmagnesium bromide prepared from 2-(3-methoxyphenyl) ethyl bromide (2.1 g. 9.77 mmol) and magnesium (300 mg, 12 mmol). The mixture was stirred at room temperature for ½ hour then quenched with saturated NH4Cl. The mixture was then extracted into EtOAc, washed with H2O, dried (Na2SO4), filtered and concentrated in vacuo, then purified by silica gel chromatography (30% EtOAc/Hexane) to provide the desired product as a colorless viscous oil. then quenched with saturated NH4Cl The mixture was then extracted into EtOAc washed with H2O dried (Na2SO4) filtered concentrated in vacuo purified by silica gel chromatography (30% EtOAc/Hexane)