Chlorosuccinimide → 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

Methyl 5-bromo-2-methylbenzoate (3 g) in ethyl acetate (100 mL) was treated with N-chlorosuccinimide (1.749 g). The mixture was stirred and heated under reflux whilst being irradiated with a halogen lamp for 5 h. The reaction mixture was cooled and washed with 10% aqueous sodium metabisufite (100 mL) and water. The organic phase was dried over magnesium sulfate and concentrated to an oil. The crude product was treated with 8M methylamine in ethanol (20 mL) and the resulting mixture heated under reflux for 30 min. After cooling, the solution was concentrated to an oil, and the mixture purified on silica gel eluting with ethyl acetate to afford the sub-titled compound (0.300 g).

1. temperatureheated
2. temperatureunder reflux
3. customwhilst being irradiated with a halogen lamp for 5 h
4. temperatureThe reaction mixture was cooled
5. washwashed with 10% aqueous sodium metabisufite (100 mL) and water
6. dry with materialThe organic phase was dried over magnesium sulfate
7. concentrationconcentrated to an oil
8. additionThe crude product was treated with 8M methylamine in ethanol (20 mL)
9. temperaturethe resulting mixture heated
10. temperatureunder reflux for 30 min
11. temperatureAfter cooling
12. concentrationthe solution was concentrated to an oil
13. customthe mixture purified on silica gel eluting with ethyl acetate

ORD record

ord-f044ff2bf4894776a71d7afacd6bb78c

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193239B2