Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(3-nitrophenyl)propiolate

Temperature

65 °C

1-Iodo-3-nitrobenzene (41.05 g, 164.3 mmol) in THF (100 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (41.27 g, 298.6 mmol), CuI (2.27 g, 11.9 mmol) and PdCl2(Ph3P)2 (1.11 g, 1.57 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (37.79 g, 149.3 mmol) in THF (68 mL) was added by syringe pump over a period of 5.4 hr, and the mixture was stirred an additional 1 h after addition was complete. After being cooled to room temperature, the mixture was filtered. The filtrate was concentrated and purified by silica gel column chromatography. The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-2 (15.96 g, 29% yield) as a brown solid.

1. additionnitrogen gas was introduced
2. stirringthe mixture was stirred an additional 1 h
3. additionafter addition
4. temperatureAfter being cooled to room temperature
5. filtrationthe mixture was filtered
6. concentrationThe filtrate was concentrated
7. custompurified by silica gel column chromatography
8. additionThe fractions containing the desired compound
9. concentrationwere concentrated
10. additionTo the concentrate added hexane
11. filtrationthe precipitated solid was collected by filtration
12. washThe solid was washed with hexane
13. customdried

ORD record

ord-6dbdfa8f095c4178bdd62a44f2c4d7f3

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416121B2