Hydrochloric Acid → HCID 23031791, compound

Temperature

25 °C

Aluminum chloride (20.4 g) was added to a solution of 3-chloro-4-methylanisole (20 g) in chlorobenzene (56 ml) at 20-30° C., and then 3-bromobenzoyl chloride (28 g) was further added dropwise over about 30 minutes at 25 to 30° C. After completion of addition, the mixture was stirred at 25° C. for 1 hour, and then heated at 40° C. for 1 hour. After the reaction was completed, the mixture was cooled, and toluene/tetrahydrofuran (1:1, 200 ml) was added dropwise at 20 to 30° C. Then, 4N hydrochloric acid (80 ml) was added dropwise. The organic layer was separated, washed successively with 2N hydrochloric acid (60 ml) and a 10% aqueous sodium chloride solution. The organic layer was concentrated to 80 g. After methanol (100 ml) was added, the mixture was concentrated again to 90 g. Methanol (80 ml) was added to the residue, the mixture was stirred at room temperature for 30 minutes, and below 5° C. for 1 hour. Crystals were collected, washed with cooled methanol (40 ml) and dried under reduced pressure to obtain the title compound (35.4 g, yield 85.1%).

1. additionAfter completion of addition
2. temperatureheated at 40° C. for 1 hour
3. temperaturethe mixture was cooled
4. customThe organic layer was separated
5. washwashed successively with 2N hydrochloric acid (60 ml)
6. concentrationThe organic layer was concentrated to 80 g
7. additionAfter methanol (100 ml) was added
8. concentrationthe mixture was concentrated again to 90 g
9. additionMethanol (80 ml) was added to the residue
10. stirringthe mixture was stirred at room temperature for 30 minutes
11. waitbelow 5° C. for 1 hour
12. customCrystals were collected
13. washwashed with cooled methanol (40 ml)
14. customdried under reduced pressure

ORD record

ord-3247996006d74cdeb926b65fa7387bb1

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541478B2