3-Bromo-5-formylbenzamide → 3-Bromo-5-formylbenzonitrile

To a solution of 3-bromo-5-formylbenzamide (1.5 g, 6.58 mmol) in H2O (50.0 mL) and MeCN (50.0 mL) was added PdCl2 (117 mg, 0.658 mmol). The mixture was stirred for 72 h at room temperature and another portion of H2O (100 mL) and MeCN (100 mL) was added followed with addition of PdCl2 (100 mg, 0.56 mol). The mixture was stirred for another 12 hr and concentrated. The residue was dissolved in EtOAc (200 mL), washed with brine (3×50.0 mL), dried over Na2SO4 and concentrated, and then was purified by chromatography (10% EtOAc in hexanes) to give 550 mg of 3-bromo-5-formylbenzonitrile (40%).

1. stirringThe mixture was stirred for another 12 hr
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in EtOAc (200 mL)
4. washwashed with brine (3×50.0 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customwas purified by chromatography (10% EtOAc in hexanes)

ORD record

ord-a6ba3257e2a3464696618ba6ec404d62

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354406B2