Boron tribromide → 2-Trifluoromethylhydroquinone

HRID 1789633Notes

Reaction equation

HRID 1789633 reaction equation
B(Br)(Br)Br.C([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)C>ClCCl>[F:16][C:15]([F:17])([F:18])[C:10]1[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][C:11]=1[OH:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 220349974-Ethoxy-2-(trifluoromethyl)phenol

Product 1

HCID 111166062-TrifluoromethylhydroquinoneYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Boron tribromide (11.8 g) was slowly added dropwise to dichloromethane (41 mL) cooled to −78° C., and then Compound (e) (6.47 g) dissolved in dichloromethane (60 mL) was slowly added dropwise at the same temperature and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into ice water and the aqueous layer was extracted with ether. The organic layers were combined, washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.53 g of Compound (g).

Workup

  1. additionwas slowly added dropwise at the same temperature
  2. extractionthe aqueous layer was extracted with ether
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3eaf5a5c4504444dad2bbf538ca8f3b7
Source dataset
uspto-grants-2006_07
Patent number
US07070838B2

Reaction notes

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