Hydrogen Bromide → 4-Bromo-2-(trifluoromethyl)benzonitrile

Temperature

0 °C

In a round bottom flask, 4-cyano-3-trifluoromethylaniline (20 g, 107.5 mmol) was solubilized in 300 mL of 47% aq HBr. This solution was cooled to 0° C. in an ice bath and NaNO2 (22.2 g, 322 mmol) was added slowly. Then CuBr (46.3 g, 322.5 mmol) was added slowly. After the addition, the ice bath was removed and the mixture was stirred at 20° C. for 3 hr. The mixture was cooled to 0° C. in an ice bath and 500 mL of water were added to get a yellow precipitate. Solid was filtered and washed successively with 10% aq. HCl (50 mL) and water (100 mL), and dried to give the product (23.5 g, 87%), 1H NMR (300 MHz, Acetone-d6)δ: 8.19 (s, 1H, C3—H), 8.16 (d, 1H, J=8 Hz, C6—H), 8.05 (d, 1H, J=8 Hz, C5—H).

1. additionAfter the addition
2. customthe ice bath was removed
3. temperatureThe mixture was cooled to 0° C. in an ice bath
4. addition500 mL of water were added
5. customto get a yellow precipitate
6. filtrationSolid was filtered
7. washwashed successively with 10% aq. HCl (50 mL) and water (100 mL)
8. customdried

ORD record

ord-50e5a16426274e3aa7a2110bd2e67238

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933321B2