3,4-Dimethylaniline → 3,4-Dimethyl-N-phenylaniline

Temperature

105 °C

Into a 250 mL round bottom flask was placed palladium acetate (120 mg) and Cytop-216 (120 mg) and was stirred in toluene (20 mL) for 1 hour at room temperature under agron. To this was added, in order, 3,4-dimethylaniline (3.27 g), bromobenzene (6 mL), sodium t-butoxide (7.9 g) and a further (20 mL) of toluene. The resulting mixture was heated at 100-110° C. for between 4 and 6 hours. The mixture was cooled to room temperature and diluted with 20 mL of toluene, filtered to remove insolubles, and 10-20 g of Al2O3 was added. The resulting slurry was heated to −80° C. and filtered while hot. The toluene was removed by rotary evaporation and the residue was recrystallized from 150 mL of isopropyl alcohol. The solid produced on cooling was filtered by suction, washed with a further 100 mL of isopropyl alcohol, and dried overnight. Yield was 5.1 g with a purity >99% which was determined by HPLC and NMR.

1. customInto a 250 mL round bottom flask was placed
2. temperatureThe mixture was cooled to room temperature
3. filtrationfiltered
4. customto remove insolubles, and 10-20 g of Al2O3
5. additionwas added
6. temperatureThe resulting slurry was heated to −80° C.
7. filtrationfiltered while hot
8. customThe toluene was removed by rotary evaporation
9. customthe residue was recrystallized from 150 mL of isopropyl alcohol
10. customThe solid produced
11. temperatureon cooling
12. filtrationwas filtered by suction
13. washwashed with a further 100 mL of isopropyl alcohol
14. customdried overnight

ORD record

ord-227e0ad1f9c1476f9f07a4247666353e

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402700B2