Methanol → 4-Bromo-2-methylbenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([CH3:10])[CH:3]=1.CC(C[Al]CC(C)C)C.CO.[OH:22]S(O)(=O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:22])=[C:4]([CH3:10])[CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To 4-bromo-2-methylbenzonitrile (2 g, 10.2 mmol) in toluene (60 mL) cooled to 5 C under argon was added Dibal-H (11.2 mL, 1M solution in toluene, 11.2 mmol) dropwise. The reaction was stirred at 5° C. for 30 minutes then MeOH (3 mL) and 2 M H2SO4 (10 mL) were added dropwise. The mixture was stirred for ˜19 h then concentrated in vacuo. The residue was re-dissolved in water/EtOAc. The organic layer was dried and concentrated to give the crude title compound as a brown oil (1.81 g) which was used in the next step without further purification. δH (CDCl3, 400 MHz) 10.20 (1H, s), 7.65 (1H, d), 7.50 (1H, dd), 7.43 (1H, m), 2.64 (3H, s).
Workup
- stirringThe mixture was stirred for ˜19 h
- concentrationthen concentrated in vacuo
- dissolutionThe residue was re-dissolved in water/EtOAc
- customThe organic layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-81ddbe3e828b4f0c8c157623c3ad84be
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700599B2
Reaction notes
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