2-ethyl-6-fluorophenol

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: A mixture of 2-fluoro-6-(1-hydroxy-ethyl)-phenol (1.7 g, 10.9 mmol) and 10 wt % Pd/C (0.85 g, Degussa type) in MeOH (30 mL) was stirred under a balloon of H2 for 6 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to a yellow oil (1.35 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3 H), 2.68 (q, J=7.3 Hz, 2 H), 5.12 (s, 1 H), 6.76 (m, 1 H), 6.92 (m, 2 H). The reaction mixture was filtered through a pad of celite washing with EtOAc The filtrate was concentrated to a yellow oil (1.35 g, 87%)

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

Procedure: A mixture of 2-fluoro-6-(1-hydroxy-ethyl)-phenol (1.7 g, 10.9 mmol) and 10 wt % Pd/C (0.85 g, Degussa type) in MeOH (30 mL) was stirred under a balloon of H2 for 6 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to a yellow oil (1.35 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3 H), 2.68 (q, J=7.3 Hz, 2 H), 5.12 (s, 1 H), 6.76 (m, 1 H), 6.92 (m, 2 H). The reaction mixture was filtered through a pad of celite washing with EtOAc The filtrate was concentrated to a yellow oil (1.35 g, 87%)

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

Procedure: A solution of tetrabutyl ammonium tribromide (4.2 g, 8.6 mmol) in CHCl3 (25 mL) was added to a stirred solution of 2-ethyl-6-fluoro-phenol (1.1 g, 7.9 mmol) dissolved in CHCl3 (25 mL). The reaction mixture was stirred for 24 hrs and then quenched with 5% solution of sodium thiosulfate (30 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (0–10% EtOAc in hexanes) to give the desired product (1 g, 60%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 5.09 (d, J=4.8 Hz, 1 H), 7.06 (s, 1 H), 7.09 (d, J=11.9 Hz, 1 H). quenched with 5% solution of sodium thiosulfate (30 mL) The biphasic mixture was stirred for 30 mins the layers were separated The organic layer was washed with 1N HCl, saturated NaHCO3, brine dried over Na2SO4 concentrated The crude residue was purified by flash column chromatography (0–10% EtOAc in hexanes)

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

Procedure: A mixture of 2-fluoro-6-(1-hydroxy-ethyl)-phenol (1.7 g, 10.9 mmol) and 10 wt % Pd/C (0.85 g, Degussa type) in MeOH (30 mL) was stirred under a balloon of H2 for 6 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to a yellow oil (1.35 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3H), 2.68 (q, J=7.3 Hz, 2H), 5.12 (s, 1H), 6.76 (m, 1H), 6.92 (m, 2H). The reaction mixture was filtered through a pad of celite washing with EtOAc The filtrate was concentrated to a yellow oil (1.35 g, 87%)

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

Procedure: A solution of tetrabutyl ammonium tribromide (4.2 g, 8.6 mmol) in CHCl3 (25 mL) was added to a stirred solution of 2-ethyl-6-fluoro-phenol (1.1 g, 7.9 mmol) dissolved in CHCl3 (25 mL). The reaction mixture was stirred for 24 hrs and then quenched with 5% solution of sodium thiosulfate (30 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (0-10% EtOAc in hexanes) to give the desired product (1 g, 60%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3H), 2.65 (q, J=7.6 Hz, 2H), 5.09 (d, J=4.8 Hz, 1H), 7.06 (s, 1H), 7.09 (d, J=11.9 Hz, 1H). quenched with 5% solution of sodium thiosulfate (30 mL) The biphasic mixture was stirred for 30 mins the layers were separated The organic layer was washed with 1N HCl, saturated NaHCO3, brine dried over Na2SO4 concentrated The crude residue was purified by flash column chromatography (0-10% EtOAc in hexanes)

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

Procedure: A mixture of 2-fluoro-6-(1-hydroxy-ethyl)-phenol (1.7 g, 10.9 mmol) and 10 wt % Pd/C (0.85 g, Degussa type) in MeOH (30 mL) was stirred under a balloon of H2 for 6 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to a yellow oil (1.35 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3 H), 2.68 (q, J=7.3 Hz, 2 H), 5.12 (s, 1 H), 6.76 (m, 1 H), 6.92 (m, 2 H). The reaction mixture was filtered through a pad of celite washing with EtOAc The filtrate was concentrated to a yellow oil (1.35 g, 87%)

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

Procedure: A solution of tetrabutyl ammonium tribromide (4.2 g, 8.6 mmol) in CHCl3 (25 mL) was added to a stirred solution of 2-ethyl-6-fluoro-phenol (1.1 g, 7.9 mmol) dissolved in CHCl3 (25 mL). The reaction mixture was stirred for 24 hrs and then quenched with 5% solution of sodium thiosulfate (30 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude residue was purified by flash column chromatography (0–10% EtOAc in hexanes) to give the desired product (1 g, 60%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3 H), 2.65 (q, J=7.6 Hz, 2 H), 5.09 (d, J=4.8 Hz, 1 H), 7.06 (s, 1 H), 7.09 (d, J=11.9 Hz, 1 H). quenched with 5% solution of sodium thiosulfate (30 mL) The biphasic mixture was stirred for 30 mins the layers were separated The organic layer was washed with 1N HCl, saturated NaHCO3, brine dried over Na2SO4 concentrated The crude residue was purified by flash column chromatography (0–10% EtOAc in hexanes)