4,4-difluoropentan-1-ol

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

Procedure: Treat a solution of 4,4-difluoropentan-1-ol (5 g, 40.3 mmol) and TsCl (8.4 g, 44.3 mmol) in DCM (80 mL) with TEA (6.1 g, 60 mmol) and DMAP (0.5 g, 4 mmol) and stir at RT overnight. Wash the mixture successively with 2M HCl, satd. NaHCO3, then brine, dry over Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet ether) to give the title compound (7.1 g, 63%). 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 4.08 (t, J=5.6 Hz, 2H), 2.47 (s, 3H), 1.94-1.84 (m, 4H), 1.57 (t, J=18.4 Hz, 3H). Wash the mixture successively with 2M HCl NaHCO3, then brine, dry over Na2SO4 concentrate purify by silica gel chromatography (EtOAc/Pet ether)

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

Procedure: Treat a solution of 4,4-difluoropentan-1-ol (5 g, 40.3 mmol) and TsCl (8.4 g, 44.3 mmol) in DCM (80 mL) with TEA (6.1 g, 60 mmol) and DMAP (0.5 g, 4 mmol) and stir at RT overnight. Wash the mixture successively with 2M HCl, satd. NaHCO3, then brine, dry over Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet ether) to give the title compound (7.1 g, 63%). 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 4.08 (t, J=5.6 Hz, 2H), 2.47 (s, 3H), 1.94-1.84 (m, 4H), 1.57 (t, J=18.4 Hz, 3H). Wash the mixture successively with 2M HCl NaHCO3, then brine, dry over Na2SO4 concentrate purify by silica gel chromatography (EtOAc/Pet ether)

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

Procedure: Treat a solution of 4,4-difluoropentan-1-ol (5 g, 40.3 mmol) and TsCl (8.4 g, 44.3 mmol) in DCM (80 mL) with TEA (6.1 g, 60 mmol) and DMAP (0.5 g, 4 mmol) and stir at RT overnight. Wash the mixture successively with 2M HCl, satd. NaHCO3, then brine, dry over Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet ether) to give the title compound (7.1 g, 63%). 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 4.08 (t, J=5.6 Hz, 2H), 2.47 (s, 3H), 1.94-1.84 (m, 4H), 1.57 (t, J=18.4 Hz, 3H). Wash the mixture successively with 2M HCl NaHCO3, then brine, dry over Na2SO4 concentrate purify by silica gel chromatography (EtOAc/Pet ether)