4-Toluenesulfonyl chloride → 3-Fluoroprop-1-yl toluene-4-sulphonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloropropanol (2.5 mL, 30 mmol), KF (3.5 g, 60 mmol) and NaI (50 mg, 0.33 mmol) in ethylene glycol (10 mL) was placed in a round-bottom flask attached to a short-path distillation condenser. The mixture was heated at 130° C. and the resulting 3-fluoropropanol was collected as a colorless liquid. To a 0° C. solution of 3-fluoropropanol (600 mg, 7.68 mmol) in pyridine (8 mL) was added tosyl chloride (3.2 g, 16.78 mmol) over 30 min. The reaction mixture was stirred at 0° C. for 4 h and quenched by adding ice-cold water and EtOAc. The product fluorotosylate was purified as described in Method 14 above to afford compound 21 (1.2 g, 67%) as a slightly yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=10.0 Hz, 1H), 7.38 (d, J=10.0 Hz, 2H), 4.59 (dt, J=50.0 & 5.0 Hz, 2H), 4.28 (dt, J=30.0 & 5.0 Hz, 2H), 2.47 (s, 3H).

Provenance & Evidence