Azobisisobutyronitrile → 2-Bromomethylphenylboronic acid

Temperature

82 °C

A suspension of 2-methylphenylboronic acid (10.65 g), N-bromosuccinimide (NBS, 16.86 g) and 2,2′-azobisisobutyronitrile (AIBN, 1.708 g) in carbon tetrachloride (1000 mL) was heated in an oil bath at 82° C. to reflux for 2 hours under anhydrous condition. Cooled the reaction mixture to room temperature and filtered off the solid. Extracted the filtrate with water (2×200 mL). The organic layer was separated, dried over MgSO4 and concentrated in vacuo to dryness. Redissolved the solid in methanol (100 mL) and added ethyl acetate (1000 mL) to it. The resultant precipitate was collected, washed with ethyl acetate (2×50 mL) and dried in the air. The filtrate was concentrated to a small volume and a second crop of solid was also collected. The combined solid was dried in an oven under high vacuum at 50° C. overnight. There was obtained 6.48 g (39%) of product.

1. temperatureto reflux for 2 hours under anhydrous condition
2. temperatureCooled the reaction mixture to room temperature
3. filtrationfiltered off the solid
4. extractionExtracted the filtrate with water (2×200 mL)
5. customThe organic layer was separated
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo to dryness
8. dissolutionRedissolved the solid in methanol (100 mL)
9. additionadded ethyl acetate (1000 mL) to it
10. customThe resultant precipitate was collected
11. washwashed with ethyl acetate (2×50 mL)
12. customdried in the air
13. concentrationThe filtrate was concentrated to a small volume
14. customa second crop of solid was also collected
15. customThe combined solid was dried in an oven under high vacuum at 50° C. overnight

ORD record

ord-0a4f066084ba4b4c925f90cb826d60e3

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06551831B2