Boron tribromide → 4-Bromo-3-isopropylphenol

HRID 841492Notes

Reaction equation

HRID 841492 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-isopropylanisole2×

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 143, 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 hours 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. temperaturewas 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-61167e8141d64491931bed4e77e55f1e
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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