Boron tribromide → 4-Bromo-3-isopropylphenol

HRID 844789Notes

Reaction equation

HRID 844789 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[CH:10]([CH3:12])[CH3:11].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117464064-Bromo-3-isopropylanisole

Product 1

HCID 225688014-Bromo-3-isopropylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-2-isopropyl-4-methoxy-benzene (Intermediate 14:3, 2.20 g, 9.60 mmols) in 50 mL CH2Cl2 at −78° C. was added BBr3 (4.81 g, 19.2 mmols; 19.2 mL of a 1M solution in CH2Cl2). After stirring for 3 hour, at −78° C. The solution was warmed to 0° C. for 3 hours and then at 25° C. for 1 hour before being quenched with H2O. The mixture was diluted with Et2O and washed with H2O and saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure. Column chromatography (2.5-10% EtOAc-hexanes) afforded the title compound as a colorless oil.

Workup

  1. temperatureThe solution was warmed to 0° C. for 3 hours
  2. customat 25° C. for 1 hour before being quenched with H2O
  3. additionThe mixture was diluted with Et2O
  4. washwashed with H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e952bca4ab2541eab2e69b6816b522be
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

Loading…