Hydrochloric Acid → 3-(2,4-Difluorophenyl)sulfanylpropan-1-ol

HRID 548755Notes

Reaction equation

HRID 548755 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

HCID 313Hydrochloric AcidHCID 576632252-[3-(2,4-Difluorophenyl)sulfanylpropoxy]oxane

Product 1

HCID 433923683-(2,4-Difluorophenyl)sulfanylpropan-1-olYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M Hydrochloric acid (10 mL) was added to a solution of 2-({3-[(2,4-difluorophenyl)thio]propyl}oxy)tetrahydro-2H-pyran (610 mg, 2.12 mmol) in methanol (10 mL) and stirred at RT for 40 minutes. The methanol was removed in vacuo and the residue adjusted to pH 6 then extracted into ethyl acetate (3×50 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a colourless oil (410 mg). 1H NMR δ (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)

Workup

  1. customThe methanol was removed in vacuo
  2. extractionthen extracted into ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-59e503cf2ada4355b89074c1f5be0ebd
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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