Methanol → (3-(Bromomethyl)phenyl)methanol
Reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](OC)=[O:7].[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=[CH:11][CH:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, to a solution of methyl 3-(bromomethyl)benzoate (10.0 g) in toluene (100 mL) was added a 1.5 M solution (100 mL) of diisobutylaluminum hydride in toluene at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added methanol at 0° C., and the resulting white precipitate was filtered off. The solvent in the filtrate was evaporated under reduced pressure to give a crude product of the title compound (8.83 g) as a colorless oil. This compound was used for the next step without further purification.
Workup
- filtrationthe resulting white precipitate was filtered off
- customThe solvent in the filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1c91de5961e448309a01d640baa274dd
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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