Hydrochloric Acid → 3-(2,4-Difluorophenyl)sulfanylpropan-1-ol
Reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[S:10][CH2:11][CH2:12][CH2:13][O:14]C1CCCCO1>CO>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[S:10][CH2:11][CH2:12][CH2:13][OH:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1M Hydrochloric acid (170 mL) was added to a solution of 2-[3-(2,4-difluorophenyl)sulfanylpropoxy]oxane (Intermediate 26) (10.8 g, 37 mmol) in methanol (170 mL) and stirred at ambient temperature for 40 minutes. The methanol was removed under reduced pressure and the remaining aqueous phase taken to pH 6. The solution was extracted with ethyl acetate (3×50 mL) and the combined organics washed with brine (50 mL), dried (MgSO4) and the solvent removed under reduced pressure to afford the product (7.5 g, 99%). 1H NMR δ (400 MHz, CDCl3): 1.38 (t, 1H), 1.83 (quintet, 2H), 2.97 (t, 2H), 3.77 (q, 2H), 6.81-6.87 (m, 2H), 7.38-7.45 (m, 1H).