4-Bromo-3-methylbenzoic acid → (4-Bromo-3-methylphenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:11]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
93 ml of a 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran are added dropwise to a solution of 10 g (46.5 mmol) of 4-bromo-3-methyl-benzoic acid in 100 ml of tetrahydrofuran at 0° C. under argon. After the reaction mixture has been heated to 20° C., it is stirred at this temperature for 16 hours. The excess borane complex is then destroyed by careful addition of water (end of the evolution of hydrogen), the mixture is extracted twice with in each case 250 ml of ethyl acetate and the combined organic phases are washed twice with in each case 100 ml of saturated sodium bicarbonate solution, water and saturated sodium chloride solution, dried over sodium sulphate and concentrated. The compound is reacted further without purification.
Workup
- customThe excess borane complex is then destroyed by careful addition of water (end of the evolution of hydrogen), the mixture
- extractionis extracted twice with in each case 250 ml of ethyl acetate
- washthe combined organic phases are washed twice with in each case 100 ml of saturated sodium bicarbonate solution, water and saturated sodium chloride solution
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- customThe compound is reacted further without purification
Sources & evidence
- ORD record
- ord-be06a72e3ec0425abf6fa3f0a75bcbea
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05863930
Reaction notes
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