Sodium Sulfite → ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

HRID 2192889Notes

Reaction equation

HRID 2192889 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1SC1CC1.ClC1C=CC=[C:28]([C:32](OO)=O)[CH:27]=1.C(=O)([O-])O.[Na+].[S:41]([O-:44])([O-])=[O:42].[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[S:41]([CH:32]1[CH2:28][CH2:27]1)(=[O:44])=[O:42]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68671827ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Product 1

HCID 68671424ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (4.57 g) was dissolved in dichloromethane (91 mL), followed by ice-cooling. To this solution was added m-chloroperbenzoic acid (5.75 g) in 5 divided portions. It was warmed to room temperature, followed by stirring for 2 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and further added a 1 M aqueous sodium sulfite solution. The organic layer was separated and the aqueous layer was then extracted with dichloromethane. The organic layer was further washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain ethyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (4.72 g) as an (E)/(Z)-mixture.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was then extracted with dichloromethane
  4. washThe organic layer was further washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec4afa313bfe4581b651e74d3c503d12
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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