1,2-Dimethoxyethane → HCID 58669121, compound

HRID 2074039Notes

Reaction equation

HRID 2074039 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.COCCOC.[F:18][C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOCC.O>[CH3:9][Si:8]([CH3:11])([CH3:10])[C:5]1[CH:6]=[CH:7][C:2]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([F:18])[C:24]=2[F:25])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 138897Silane, (4-bromophenyl)trimethyl-HCID 2734333(2,3-Difluorophenyl)boronic acid

Product 1

HCID 58669121HCID 58669121, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  1. additionwas added
  2. customa reaction for about 10 hours
  3. temperatureAfter being cooled to room temperature
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-12b422077d9941eeb5d6025c2e75b642
Source dataset
uspto-grants-2011_04
Patent number
US07919008B2

Reaction notes

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