2-(4-bromo-2-fluorophenyl)ethanamine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H). treated with 1.0 M The reaction was heated to reflux overnight quenched with H2O extracted with ether (3×) The aqueous layer was then extracted into ether (3×) The combined organic layers were washed with brine dried over Na2SO4 filtered concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia