[2-(Bromomethyl)-3-chlorophenyl]methanol → 2-(Bromomethyl)-3-chlorobenzaldehyde

Dichloromethane (15 ml) and manganese dioxide (1.69 g, 19.4 mmol) were added to [2-(bromomethyl)-3-chlorophenyl]methanol obtained in Example 10d (440 mg, 1.87 mmol), followed by stirring at mom temperature overnight. Manganese dioxide (1.2 g, 13.8 mmol) was further added, followed by heating with stirring at 40° C. for 2.5 hours. The reaction mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the resulting crude product was purified by column chromatography (silica gel, elution solvent: heptane/ethyl acetate=99/1->90/10) to give the title compound (289 mg, yield 66.2%).

1. temperatureby heating
2. stirringwith stirring at 40° C. for 2.5 hours
3. filtrationThe reaction mixture was filtered through Celite
4. washwashed with ethyl acetate
5. concentrationThe filtrate was concentrated under reduced pressure
6. customthe resulting crude product was purified by column chromatography (silica gel, elution solvent: heptane/ethyl acetate=99/1->90/10)

ORD record

ord-5232bbafd6294d8ca966fae313deae3c

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476301B2