4-bromo-3-(bromomethyl)benzonitrile

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 of 4-bromo-3-methylbenzonitrile (1.0 g, 5.0 mmol) in carbon tetrachloride (7.5 mL) was added N-bromosuccinimide (1.0 g, 5.6 mmol) followed by of benzoylperoxide (50 mg 0.2 mmol) and the mixture was refluxed. After 10 hours, the reaction was cooled to rt, filtered, and the filtrate was washed with 10% NaHSO3 (5 mL) followed by water (5 mL). The organic layer was dried (Na2SO4), filtered, volatiles removed, and the residue was purified by flash chromatography on silica gel. Elution with 10% Ethyl acetate in hexanes gave the title compound (0.5 g, 36%) as a white solid. 1H NMR (270 MHz, CDCl3) δ4.55 (s, 2 H), 7.38-7.42 (m, 1 H), 7.65-7.77 (m, 2H). the mixture was refluxed filtered the filtrate was washed with 10% NaHSO3 (5 mL) The organic layer was dried (Na2SO4) filtered volatiles removed the residue was purified by flash chromatography on silica gel Elution with 10% Ethyl acetate in hexanes

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

Procedure: To a solution of of 4-bromo-3-methylbenzonitrile (1.0 g, 5.0 mmol) in carbon tetrachloride (7.5 mL) was added N-bromosuccinimide (1.0 g, 5.6 mmol) followed by of benzoylperoxide (50 mg 0.2 mmol) and the mixture was refluxed. After 10 hours, the reaction was cooled to rt, filtered, and the filtrate was washed with 10% NaHSO3 (5 mL) followed by water (5 mL). The organic layer was dried (Na2SO4), filtered, volatiles removed, and the residue was purified by flash chromatography on silica gel. Elution with 10% Ethyl acetate in hexanes gave the title compound (0.5 g, 36%) as a white solid. 1H NMR (270 MHz, CDCl3) δ4.55 (s, 2 H), 7.38-7.42 (m, 1 H), 7.65-7.77 (m, 2H). the mixture was refluxed filtered the filtrate was washed with 10% NaHSO3 (5 mL) The organic layer was dried (Na2SO4) filtered volatiles removed the residue was purified by flash chromatography on silica gel Elution with 10% Ethyl acetate in hexanes

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

Procedure: To a solution of of 4-bromo-3-methylbenzonitrile (1.0 g, 5.0 mmol) in carbon tetrachloride (7.5 mL) was added N-bromosuccinimide (1.0 g, 5.6 mmol) followed by of benzoylperoxide (50 mg 0.2 mmol) and the mixture was refluxed. After 10 hours, the reaction was cooled to rt, filtered, and the filtrate was washed with 10% NaHSO3 (5 mL) followed by water (5 mL). The organic layer was dried (Na2SO4), filtered, volatiles removed, and the residue was purified by flash chromatography on silica gel. Elution with 10% Ethyl acetate in hexanes gave the title compound (0.5 g, 36%) as a white solid. 1H NMR (270 MHz, CDCl3) δ4.55 (s, 2 H), 7.38-7.42 (m, 1 H), 7.65-7.77 (m, 2H). the mixture was refluxed filtered the filtrate was washed with 10% NaHSO3 (5 mL) The organic layer was dried (Na2SO4) filtered volatiles removed the residue was purified by flash chromatography on silica gel Elution with 10% Ethyl acetate in hexanes

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 4-bromo-3-(bromomethyl)benzonitrile (0.9 g, 3.27 mmol) in DMF (13.09 ml) was added (S)-3-methylmorpholine (0.541 g, 3.93 mmol) and potassium carbonate (0.995 g, 7.20 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was poured onto water and extracted with EtOAc (×2). The organic extractions were combined, washed with brine (×3), dried (MgSO4) and evaporated to give the sub-title compound as a yellow oil. Yield: 0.75 g The reaction mixture was poured onto water extracted with EtOAc (×2) The organic extractions washed with brine (×3) dried (MgSO4) evaporated

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

Procedure: To a solution of 4-bromo-3-(bromomethyl)benzonitrile (0.9 g, 3.27 mmol) in DMF (13.09 ml) was added (S)-3-methylmorpholine (0.541 g, 3.93 mmol) and potassium carbonate (0.995 g, 7.20 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was poured onto water and extracted with EtOAc (×2). The organic extractions were combined, washed with brine (×3), dried (MgSO4) and evaporated to give the sub-title compound as a yellow oil. Yield: 0.75 g The reaction mixture was poured onto water extracted with EtOAc (×2) The organic extractions washed with brine (×3) dried (MgSO4) evaporated

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

Procedure: To a solution of 4-bromo-3-(bromomethyl)benzonitrile (0.95 g, 3.46 mmol) in DMF (13.40 ml) was added thiomorpholine (0.417 ml, 4.15 mmol) and potassium carbonate (0.573 g, 4.15 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was poured onto water and extracted with EtOAc (×2). The organic extractions were combined, washed with brine (×3), dried (MgSO4) and evaporated to give a yellow oil. This was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane) to give the sub-title compound as a colourless oil. Yield: 0.951 g The reaction mixture was poured onto water extracted with EtOAc (×2) The organic extractions washed with brine (×3) dried (MgSO4) evaporated to give a yellow oil This was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane)

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

Procedure: To a solution of 4-bromo-3-(bromomethyl)benzonitrile (0.95 g, 3.46 mmol) in DMF (13.40 ml) was added thiomorpholine (0.417 ml, 4.15 mmol) and potassium carbonate (0.573 g, 4.15 mmol). The reaction mixture was allowed to stir at RT overnight. The reaction mixture was poured onto water and extracted with EtOAc (×2). The organic extractions were combined, washed with brine (×3), dried (MgSO4) and evaporated to give a yellow oil. This was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane) to give the sub-title compound as a colourless oil. Yield: 0.951 g The reaction mixture was poured onto water extracted with EtOAc (×2) The organic extractions washed with brine (×3) dried (MgSO4) evaporated to give a yellow oil This was purified by flash silica chromatography (Biotage column) (eluent=25% ether/isohexane)

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

Procedure: To a solution of of 4-bromo-3-methylbenzonitrile (1.0 g, 5.0 mmol) in carbon tetrachloride (7.5 mL) was added N-bromosuccinimide (1.0 g, 5.6 mmol) followed by of benzoylperoxide (50 mg 0.2 mmol) and the mixture was refluxed. After 10 hours, the reaction was cooled to rt, filtered, and the filtrate was washed with 10% NaHSO3 (5 mL) followed by water (5 mL). The organic layer was dried (Na2SO4), filtered, volatiles removed, and the residue was purified by flash chromatography on silica gel. Elution with 10% Ethyl acetate in hexanes gave the title compound (0.5 g, 36%) as a white solid. 1H NMR (270 MHz, CDCl3) δ 4.55 (s, 2H), 7.38-7.42 (m, 1H), 7.65-7.77 (m, 2H). the mixture was refluxed filtered the filtrate was washed with 10% NaHSO3 (5 mL) The organic layer was dried (Na2SO4) filtered volatiles removed the residue was purified by flash chromatography on silica gel Elution with 10% Ethyl acetate in hexanes