2-bromo-4-fluoro-1-(2-iodoethyl)benzene

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.23 g, 6.78 mmol) in toluene (15 ml) was added Ph3P (1.778 g, 6.78 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was cooled to rt, solids were filtered and washed with toluene and ether, dried under high vac to afford (2-bromo-4-fluorophenethyl)triphenylphosphonium, iodide salt (3 g, 5.07 mmol, 74.8% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.01-7.87 (m, 9H), 7.85-7.77 (m, 6H), 7.66-7.51 (m, 1H), 7.35-7.24 (m, 1H), 7.20-7.07 (m, 1H), 3.93-3.80 (m, 2H), 3.07-2.86 (m, 2H). The mixture was cooled to rt solids were filtered washed with toluene and ether dried under high vac

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.23 g, 6.78 mmol) in toluene (15 ml) was added Ph3P (1.778 g, 6.78 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was cooled to rt, solids were filtered and washed with toluene and ether, dried under high vac to afford (2-bromo-4-fluorophenethyl)triphenylphosphonium, iodide salt (3 g, 5.07 mmol, 74.8% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.01-7.87 (m, 9H), 7.85-7.77 (m, 6H), 7.66-7.51 (m, 1H), 7.35-7.24 (m, 1H), 7.20-7.07 (m, 1H), 3.93-3.80 (m, 2H), 3.07-2.86 (m, 2H). The mixture was cooled to rt solids were filtered washed with toluene and ether dried under high vac

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:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.23 g, 6.78 mmol) in toluene (15 ml) was added Ph3P (1.778 g, 6.78 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was cooled to rt, solids were filtered and washed with toluene and ether, dried under high vac to afford (2-bromo-4-fluorophenethyl)triphenylphosphonium, iodide salt (3 g, 5.07 mmol, 74.8% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.01-7.87 (m, 9H), 7.85-7.77 (m, 6H), 7.66-7.51 (m, 1H), 7.35-7.24 (m, 1H), 7.20-7.07 (m, 1H), 3.93-3.80 (m, 2H), 3.07-2.86 (m, 2H). The mixture was cooled to rt solids were filtered washed with toluene and ether dried under high vac

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)