Sodium Carbonate → 2-[2-(2-Bromophenylsulfanyl)ethoxy]tetrahydropyran

HRID 1012349Notes

Reaction equation

HRID 1012349 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].Br[CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 805982-BromobenzenethiolHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 231526382-[2-(2-Bromophenylsulfanyl)ethoxy]tetrahydropyranYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromobenzenethiol (3.0 ml, 24.9 mmol) in N,N-dimethylformamide (50 ml) was added sodium hydride (60% in oil, 1.10 g, 27.5 mmol) under ice-cooling, and the mixture was stirred for 1 hr. To this reaction mixture was added 2-(2-bromoethoxy)tetrahydropyran (4.5 ml, 29.7 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Aqueous sodium carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give 2-[2-(2-bromophenylsulfanyl)ethoxy]tetrahydropyran (7.91 g, yield 100%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was successively washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-14241e1820aa471ab8bb05290e18c2c3
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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