반응 #1247198

반응 방정식

2,4-dichloro-5-fluoropyrimidine

1-bromo-3-ethynylbenzene

→

desired product

수율 80.2%

4-[(3-Bromophenyl)ethynyl]-2-chloro-5-fluoropyrimidine

수율 80.2%

용매

THF

THF

반응 조건

후처리

1. 1
   온도After heating
2. 2
   기타the reaction at 60° C. for 30 min
3. 3
   온도to heat overnight
4. 4
   기타The crude reaction mixture
5. 5
   기타purified by column chromatography (2-10% EtOAc in hexanes)

실험 절차

To an oven-dried flask under N2 was added 2,4-dichloro-5-fluoropyrimidine (1.66 g, 10 mmol), anhydrous, degassed THF (100 mL), dichlorobis(triphenyl-phosphine)palladium(II) (180 mg, 0.26 mmol), copper(I) iodide (29 mg, 0.15 mmol), and TEA (2.02 g, 20 mmol). After heating the reaction at 60° C. for 30 min, 1-bromo-3-ethynylbenzene (0.9 g, 5.0 mmol) was added dropwise as a solution in THF (25 mL) and the resulting mixture was allowed to heat overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (2-10% EtOAc in hexanes) to afford the desired product (1.25 g, 78%) as an off white solid. ESIMS (M+H)+=311.

출처