Triphosgene → 1-Chloro-2-fluoro-4-isocyanato-benzene

Temperature

0 °C

4-Chloro-3-fluoroaniline (2 g, 13.7 mmol) was dissolved in 60 mL of dichloromethane. Under ice bath, saturated sodium bicarbonate solution (60 mL) was added. The mixture was stirred at 0° C. and triphosgene (1.36 g, 4.58 mmol) was added. The mixture was stirred at 0° C. for 1 h and then extracted with dichloromethane and water. The organic layer was dried with sodium sulfate and filtered. The filtrate solution was concentrated and the residue was treated with 50 mL of hexanes. The hexane solution was concentrated to remove all solvents. The residue was taken up in 12 mL of hexanes and filtered. The solution was concentrated and dried to give 1-chloro-2-fluoro-4-isocyanatobenzene as an off white solid (1.69 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 6.82-6.90 (m, 1H) 6.93 (dd, J=9.22, 2.65 Hz, 1H) 7.31-7.41 (m, 1H).

1. stirringThe mixture was stirred at 0° C. for 1 h
2. extractionextracted with dichloromethane and water
3. dry with materialThe organic layer was dried with sodium sulfate
4. filtrationfiltered
5. concentrationThe filtrate solution was concentrated
6. additionthe residue was treated with 50 mL of hexanes
7. concentrationThe hexane solution was concentrated
8. customto remove all solvents
9. filtrationfiltered
10. concentrationThe solution was concentrated
11. customdried

ORD record

ord-91eb8d480c9143118d5e28d9bb5ccaf5

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353096B2