4-Methoxybenzenethiol → (2,2-Dimethoxyethyl)(4-methoxyphenyl)sulfane

HRID 500123Notes

Reaction equation

HRID 500123 reaction equation
[O-]CC.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1.Br[CH2:15][CH:16]([O:19][CH3:20])[O:17][CH3:18]>C(O)C>[CH3:18][O:17][CH:16]([O:19][CH3:20])[CH2:15][S:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 127654-MethoxybenzenethiolHCID 816722-Bromo-1,1-dimethoxyethaneHCID 2723922Sodium ethoxide

Product 1

HCID 14175762(2,2-Dimethoxyethyl)(4-methoxyphenyl)sulfaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice cooled solution of sodium ethoxide (3.26 g, 48.0 mmol) in ethanol (25.0 mL) was slowly added 4-methoxybenzenethiol (6.73 g, 48.0 mmol). The reaction mixture was stirred for 15 min. 2-Bromo-1,1-dimethoxyethane (5.64 mL, 48.0 mmol) was added, and the reaction mixture was refluxed for 2 h. After the precipitate was isolated by filtration, the mother liquor was evaporated under reduced pressure. The resultant residue was diluted with diethyl ether (100 mL) and washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give the desired crude product (11.0 g) which was directly used in next step reaction without further purification. 1H-NMR (400 MHz, CDCl3): 7.40 (m, 2H), 6.85 (m, 2H), 4.47 (t, J=5.6 Hz, 1H), 3.80 (s, 3H), 3.34 (s, 6H), 3.01 (d, J=5.6 Hz, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customAfter the precipitate was isolated by filtration
  3. customthe mother liquor was evaporated under reduced pressure
  4. additionThe resultant residue was diluted with diethyl ether (100 mL)
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2048632d579343fb8c8d35243b33bcd8
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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