Ethyl Acetate → (2-Bromo-5-ethoxy-4-methylphenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([O-])=[O:5].CC(C[AlH]CC(C)C)C.CCOC(C)=O>CCOCC>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH2:13][CH3:14])=[CH:7][C:3]=1[CH2:4][OH:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-bromo-5-ethoxy-4-methylbenzoate (660 mg, 2.23 mmol) in ether (20 mL) at 0° C. was added DIBAL (5.75 mL, 5.75 mmol, 1 M in toluene). The reaction was stirred at 0° C. for 10 minutes. EtOAc (20 mL) and wet silica gel (˜50 g silica gel and 3 mL of water) were added portion wise at 0° C. The resulting slurry was stirred for ˜15 minutes and was filtered, washed with EtOAc (20 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with EtOAc/hexanes (20/80) to give the title intermediate (550 mg) as colorless liquid.
Workup
- stirringThe resulting slurry was stirred for ˜15 minutes
- filtrationwas filtered
- washwashed with EtOAc (20 mL)
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on a silica gel column
- washeluting with EtOAc/hexanes (20/80)
Sources & evidence
- ORD record
- ord-13f7f37a386f4f338cfb418d935bb65f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742110B2
Reaction notes
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