Boron tribromide → HCID 22737361, compound

HRID 843629Notes

Reaction equation

HRID 843629 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]1([CH3:16])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18414650HCID 18414650, compound

Product 1

HCID 22737361HCID 22737361, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(4,4-dimethylcyclohexyl)anisole (2.76 g, 12.64 mmol), boron tribromide (4.42 mL, 15.2 mmol), in methylene chloride was stirred at room temperature overnight. The reaction mixture was treated with wet ice and diluted with methylene chloride. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The product was chromatographed on silica gel, using a toluene/ethyl acetate (18:1), to afford the title compound (2.19 g).

Workup

  1. additionThe reaction mixture was treated with wet ice
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-ec03254a535b413d9434154ac4e1e44c
Source dataset
uspto-grants-2002_04
Patent number
US06380191B1

Reaction notes

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