Sodium Thiosulfate → 2-bromo-1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone

HRID 1257357Notes

Reaction equation

HRID 1257357 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br-:18].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C>[Br:18][CH2:16][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=1)=[O:17]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 143614891-(3-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 116456082-bromo-1-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution (40 mL) of the compound (9.4 g, 37 mmol) obtained in Example 38a in diethyl ether was added phenyltrimethylammonium tribromide (14 g, 37 mmol), and the mixture was stirred at room temperature for 5 hr. After confirmation of the termination of the reaction by TLC, aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude title compound as a colorless oil.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-54a7c394510e48d29995ed5f9065b186
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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