2-(2-bromo-4-fluorophenyl)ethanol

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

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

Procedure: A solution of Ph3P (2.57 g, 9.81 mmol) and imidazole (0.668 g, 9.81 mmol) in DCM (50 mL) was cooled to 0° C. Added to this was iodine (2.489 g, 9.81 mmol) and the resulting mixture was stirred at 0° C. for 30 min. 2-(2-Bromo-4-fluorophenyl)ethanol (1.79 g, 8.17 mmol) was added portionwise over several minutes and the resulting mixture was stirred at room temp. After 16 h, the mixture was filtered washing the solids with DCM. The filtrate was washed with aq Na2S2O3 and the organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV) to give 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.4 g, 7.30 mmol, 89% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.2, 2.7 Hz, 1H), 7.25 (dd, J=8.5, 5.8 Hz, 1H), 7.02 (td, J=8.2, 2.6 Hz, 1H), 3.41-3.35 (m, 2H), 3.32-3.26 (m, 2H). the resulting mixture was stirred at room temp After 16 h the mixture was filtered washing the solids with DCM The filtrate was washed with aq Na2S2O3 the organic phase was dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV)

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

Procedure: To a solution of 2-(2-bromo-4-fluorophenyl)acetic acid (2.3 g, 9.87 mmol) in THF (20 mL) at 0° C. was added 1M BH3.THF comples (14.80 mL, 14.80 mmol) in THF and the resulting mixture was stirred at room temp for 3 h. 1N HCl (50 mL) was then added and the mixture was extracted with ethyl acetate (200 mL), washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to afford 2-(2-bromo-4-fluorophenyl)ethanol (2.0 g, 9.13 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.4, 2.7 Hz, 1H), 7.30-7.24 (m, 1H), 7.01 (td, J=8.2, 2.6 Hz, 1H), 3.89 (q, J=6.6 Hz, 2H), 3.02 (t, J=6.6 Hz, 2H), 1.43 (t, J=5.8 Hz, 1H). the mixture was extracted with ethyl acetate (200 mL) washed with brine (50 mL) dried (Na2SO4) filtered concentrated

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

Procedure: To a solution of (2-bromo-4-fluorophenyl)acetic acid (1.5 g, 6.44 mmol) in tetrahydrofuran (10 mL) was added 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (9.66 mL, 9.66 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL), extracted with ethyl acetate (200 mL). The organic layer washed with brine (50 mL) dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1) to afford 1.30 g (92%) of the title compound as colorless oil: The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL) extracted with ethyl acetate (200 mL) The organic layer washed with brine (50 mL) dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1)

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

Procedure: To a solution of (2-bromo-4-fluorophenyl)acetic acid (1.5 g, 6.44 mmol) in tetrahydrofuran (10 mL) was added 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (9.66 mL, 9.66 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL), extracted with ethyl acetate (200 mL). The organic layer washed with brine (50 mL) dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1) to afford 1.30 g (92%) of the title compound as colorless oil: The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL) extracted with ethyl acetate (200 mL) The organic layer washed with brine (50 mL) dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1)

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 (2-bromo-4-fluorophenyl)acetic acid (1.5 g, 6.44 mmol) in tetrahydrofuran (10 mL) was added 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (9.66 mL, 9.66 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL), extracted with ethyl acetate (200 mL). The organic layer was washed with brine (50 mL) dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1) to afford 1.30 g (92%) of the title compound as colorless oil: The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL) extracted with ethyl acetate (200 mL) The organic layer was washed with brine (50 mL) dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1)

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

Procedure: A solution of Ph3P (2.57 g, 9.81 mmol) and imidazole (0.668 g, 9.81 mmol) in DCM (50 mL) was cooled to 0° C. Added to this was iodine (2.489 g, 9.81 mmol) and the resulting mixture was stirred at 0° C. for 30 min. 2-(2-Bromo-4-fluorophenyl)ethanol (1.79 g, 8.17 mmol) was added portionwise over several minutes and the resulting mixture was stirred at room temp. After 16 h, the mixture was filtered washing the solids with DCM. The filtrate was washed with aq Na2S2O3 and the organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV) to give 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.4 g, 7.30 mmol, 89% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.2, 2.7 Hz, 1H), 7.25 (dd, J=8.5, 5.8 Hz, 1H), 7.02 (td, J=8.2, 2.6 Hz, 1H), 3.41-3.35 (m, 2H), 3.32-3.26 (m, 2H). the resulting mixture was stirred at room temp After 16 h the mixture was filtered washing the solids with DCM The filtrate was washed with aq Na2S2O3 the organic phase was dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV)

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

Procedure: To a solution of 2-(2-bromo-4-fluorophenyl)acetic acid (2.3 g, 9.87 mmol) in THF (20 mL) at 0° C. was added 1M BH3.THF comples (14.80 mL, 14.80 mmol) in THF and the resulting mixture was stirred at room temp for 3 h. 1N HCl (50 mL) was then added and the mixture was extracted with ethyl acetate (200 mL), washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to afford 2-(2-bromo-4-fluorophenyl)ethanol (2.0 g, 9.13 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.4, 2.7 Hz, 1H), 7.30-7.24 (m, 1H), 7.01 (td, J=8.2, 2.6 Hz, 1H), 3.89 (q, J=6.6 Hz, 2H), 3.02 (t, J=6.6 Hz, 2H), 1.43 (t, J=5.8 Hz, 1H). the mixture was extracted with ethyl acetate (200 mL) washed with brine (50 mL) dried (Na2SO4) filtered concentrated

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

Procedure: To a solution of (2-bromo-4-fluorophenyl)acetic acid (1.5 g, 6.44 mmol) in tetrahydrofuran (10 mL) was added 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (9.66 mL, 9.66 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL), extracted with ethyl acetate (200 mL). The organic layer washed with brine (50 mL) dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1) to afford 1.30 g (92%) of the title compound as colorless oil: The reaction mixture was quenched by the addition of 2N hydrochloric acid (50 mL) extracted with ethyl acetate (200 mL) The organic layer washed with brine (50 mL) dried over sodium sulfate evaporated The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (5/1)

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