Azobisisobutyronitrile → 1,3-Dibromo-2-(bromomethyl)benzene

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was purged with nitrogen and charged with 2,6-dibromotoluene (2.50 g, 10.0 mmol), N-bromosuccinimide (1.78 g, 10.0 mmol) and carbon tetrachloride (40 mL). The solution was heated to 80° C. (oil bath temperature), and 2,2′-azobisisobutyronitrile (164 mg, 1.00 mmol) was added. The resulting mixture was refluxed for 14 h. After that time, the mixture was cooled to room temperature and filtered. The filter cake was washed with carbon tetrachloride (2×20 mL). The filtrate was diluted with ethyl acetate (200 mL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford a quantative yield (3.28 g) of 1,3-dibromo-2-(bromomethyl)benzene as a yellow solid: mp 77-78° C.; 1H NMR (300 MHz, CDCl3) d 7.55 (d, 2H, J=8.1 Hz), 7.07 (t, 1H, J=8.1 Hz), 4.83 (s, 2H)

1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
2. temperaturereflux condenser and nitrogen inlet
3. customwas purged with nitrogen
4. additionwas added
5. temperatureThe resulting mixture was refluxed for 14 h
6. filtrationfiltered
7. washThe filter cake was washed with carbon tetrachloride (2×20 mL)
8. additionThe filtrate was diluted with ethyl acetate (200 mL)
9. washwashed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL)
10. dry with materialThe organic layer was dried over sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customto afford

ORD record

ord-b820ac2a8a154bffa6fb9e6459a44651

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618107B2