Réaction #2161221

Équation de réaction

1-bromo-4-trimethylsilylbenzene

DME

2,3-difluorophenylboronic acid

Na2CO3

→

4′-trimethylsilyl-2,3-difluorobiphenyl

Rendement 91.0%

Solvants

ether

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Autrea reaction for about 10 hours
3. 3
   TempératureAfter being cooled to room temperature
4. 4
   Autrepurified by silica gel column chromatography

Mode opératoire

First, 7.9 g of 1-bromo-4-trimethylsilylbenzene was dissolved into 86 ml of DME, and 6.5 g of 2,3-difluorophenylboronic acid, 1.2 g of tetrakis(triphenylphosphine)palladium (0) and 86 ml of 2.0M Na2CO3 was added thereto. Next, the reaction mixture was heated to 100° C. to perform a reaction for about 10 hours. After being cooled to room temperature, the reaction mixture was worked up with water and ether, and then purified by silica gel column chromatography to obtain the 4′-trimethylsilyl-2,3-difluorobiphenyl compound with a yield of 91%. Then, 3.0 g of the biphenyl compound was dissolved into 20 ml of dry THF under nitrogen atmosphere, and 5.0 ml of 2.5M n-BuLi was added thereto at −78° C. to form an anion over about 3 hours. Then, 2.0 ml of 4-n-propylcyclohexanone was added to the anion, and the reaction mixture was warmed gradually to room temperature. After stirring at room temperature for 2 hours, the reaction mixture was worked up with water and ether, and evaporated under reduced pressure, and then dissolved into CH2Cl2 solvent. Next, 1.0 g of TsOH was added thereto, and the reaction mixture was allowed to react at 60° C. for 10 hours. After the completion of the reaction, the reaction mixture was purified by silica gel column chromatography to obtain the silicon-containing compound (yield: 80%). 400 MHz 1H-NMR, CDCl3, δ (ppm): 0.38 (s, 9H), 0.97 (m, 3H), 1.34˜1.46 (m, 5H), 1.63˜1.76 (br, 1H), 1.84˜1.98 (m, 2H), 2.33˜2.59 (m, 3H), 6.06 (br, 1H), 7.05˜7.12 (m, 1H), 7.12˜7.18 (m, 1H), 7.56 (d, 2H), 7.63 (d, 2H).

Source