Diisobutylaluminum hydride → HCID 77230761, compound
Reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11](N(OC)C)=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH:11]=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of Compound 7-bromo-N-methoxy-N-methyl-1-benzofuran-3-carboxamide (8.98 g, 31.63 mmol) in 150 mL dry toluene at −78° C. was added DIBAL-H (31.63 mL, 31.63 mmol) dropwise. The reaction mixture was stirred for 1 hour at −78° C. under a nitrogen atmosphere, and quenched slowly with saturated aqueous NH4Cl. After warming to room temperature, the mixture was exacted with EtOAc (300 mL), and washed with brine (50 mL), dried over Na2SO4. The solvent was concentrated in vacua. The residue was separated and purified with silica gel chromatography to give product 7-bromo-1-benzofuran-3-carbaldehyde.