3-Chlorothiophenol → 1-Chloro-3-[(2,2-dimethoxyethyl)sulfanyl]benzene

HRID 1432838Notes

Reaction equation

HRID 1432838 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12]Br.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:12][CH:11]([O:14][CH3:15])[O:10][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 162573-ChlorothiophenolHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 181763361-Chloro-3-[(2,2-dimethoxyethyl)sulfanyl]benzeneYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chlorothiophenol (2.4 g, 16.6 mmol) in THF (200 mL) at 0° C. is added bromoacetaldehyde dimethyl acetal (2.8 g, 16.6 mmol). To the solution is added sodium hydride (60% mineral oil dispersion, 0.70 g, 17.4 mmol). The reaction is stirred for 16 hours, and then is quenched by the addition of saturated NH4Cl (aq.). The solution is diluted with EtOAc. The organic layer is washed with a saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes. The title compound (3.7 g, 15.9 mmol) is obtained as an oil. 1H NMR (CDCl3, 300 MHz) δ7.32 (m, 1H), 7.25 (m, 1H), 7.12 (m, 1H), 4.47 (m, 1H), 3.07 (s, 3H), 3.02 (s, 3H).

Workup

  1. customis quenched by the addition of saturated NH4Cl (aq.)
  2. additionThe solution is diluted with EtOAc
  3. washThe organic layer is washed with a saturated NaCl (aq.)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography
  8. washeluting with hexanes

Sources & evidence

ORD record
ord-202487eb3e4441d1beb7d77eade3d07a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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