Water → 4-Bromo-2-chloro-1-(propan-2-yl)benzene

HRID 70574Notes

Reaction equation

HRID 70574 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](O)([CH3:24])[CH3:23])=[C:18]([Cl:26])[CH:17]=1.O>ClCCl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:23])[CH3:24])=[C:18]([Cl:26])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58764285875307-00-9

Product 1

HCID 595964524-Bromo-2-chloro-1-(propan-2-yl)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (1.8 mL) and trifluoroacetic acid (5.8 mL) were added to a solution of 2-(4-bromo-2-chlorophenyl)propan-2-ol (1.9 g) in dichloromethane (76 mL), and the mixture was stirred at room temperature for one day. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (1.74 g, 98%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane only)

Sources & evidence

ORD record
ord-34f6247782814de99e36a2e5ca7f4dd4
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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