Diisobutylaluminum hydride → 4-Bromo-2,6-dimethylbenzaldehyde

DIBAL-H (1.0M in hexanes; 22.0 mL, 22.0 mmol) was added to a solution of 4-bromo-2,6-dimethylbenzonitrile (3.87 g, 18 mmol) in CH2Cl2 (50 mL) at 0° C., and the resulting mixture stirred at 25° C. for 3 h. Saturated aqueous sodium potassium tartrate solution (75 mL) was then slowly added, and the resulting mixture was stirred vigorously for 30 min. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-20% EtOAc/hexanes) furnished 4-bromo-2,6-dimethylbenzaldehyde as a light brown solid.

1. stirringthe resulting mixture was stirred vigorously for 30 min
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with CH2Cl2)
4. dry with materialThe combined organic extracts were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customChromatographic purification of the residue (silica gel, 0-20% EtOAc/hexanes)

ORD record

ord-b07de9ef1e7845448be588a71069844b

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2