Boron tribromide → 4-Bromo-3-isopropylphenol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas warmed to 0° C. for 3 hours
- customat 25° C. for 1 hour before being quenched with H2O
- additionThe mixture was diluted with Et2O
- washwashed with H2O and saturated aqueous NaCl
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6d0500634ae74634b30e3ea35b77a5a1
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713647B2
Reaction notes
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