Water → N-(4-bromophenyl)-3-(trifluoromethyl)benzamide

Under a nitrogen atmosphere, 4-bromoaniline (15.75 g, 91.6 mmol) was dissolved in anhydrous dichloromethane (220 ml) in a 500-ml flask. Triethylamine (14.1 ml, 100 mmol) was added to the solution. The mixture was cooled in an ice bath and 3-(trifluoromethyl)benzoyl chloride (21 g, 100 mmol) was added slowly through a syringe. The reaction mixture was allowed to warm to room temperature with stirring overnight. Deionized water was added to the mixture and the solution was transferred to a separatory funnel. The organic layer was separated and washed one more time with deionized water. The water was discarded, and the organic layer contained a suspension that was collected and heated to 40° C. to afford dissolution. After cooling to room temperature, a solid formed. The solid was collected by filtration and was triturated in dichloromethane (100 ml). The solid was then filtered and dried under high vacuum oven at 65° C. Pure product was obtained (28 g, 90% yield). M/Z of [M−H]−=343. 1H NMR (DMSO) δ=7.6 (2H), 7.8 (3H), 7.95 (1H), 8.3(1H), 10.6 (1H).

1. temperatureThe mixture was cooled in an ice bath
2. customthe solution was transferred to a separatory funnel
3. customThe organic layer was separated
4. washwashed one more time with deionized water
5. customwas collected
6. temperatureheated to 40° C.
7. customto afford
8. dissolutiondissolution
9. temperatureAfter cooling to room temperature
10. customa solid formed
11. filtrationThe solid was collected by filtration
12. customwas triturated in dichloromethane (100 ml)
13. filtrationThe solid was then filtered
14. customdried under high vacuum oven at 65° C
15. customPure product was obtained (28 g, 90% yield)

ORD record

ord-a687510de40c495aa664b132243ee52b

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119120B2