1-Ethynyl-4-propylcyclohexane → 1-Ethoxy-2,3-difluoro-4-(4-propylcyclohexylethynyl)benzene

HRID 1841829노트

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HRID 1841829 반응식
[C:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4]1)#[CH:2].Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([F:22])[C:14]=1[F:23]>C(N(CC)CC)C.CC(OC)(C)C.Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:2]#[C:1][CH:3]2[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4]2)=[C:14]([F:23])[C:15]=1[F:22])[CH3:21]

참가 물질

8

반응물 2

HCID 218706261-Ethynyl-4-propylcyclohexaneHCID 269854911-Bromo-4-ethoxy-2,3-difluorobenzene

생성물 1

HCID 199845241-Ethoxy-2,3-difluoro-4-(4-propylcyclohexylethynyl)benzene

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 313Hydrochloric Acid용매HCID 8471Triethylamine용매HCID 15413tert-Butyl methyl ether용매

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온도
50 °C

실험 절차

A mixture of 20.6 g (0.14 mol) of 1-ethynyl-4-propylcyclohexane, 25.0 g (0.11 mol) of 1-bromo-4-ethoxy-2,3-difluorobenzene, 2.22 g (3.16 mmol) of bis(triphenylphosphine)palladium(II) chloride and 603 mg (3.16 mmol) of copper(I) iodide in 440 ml of triethylamine is warmed at 50° C. for 19 h. After cooling, the mixture is diluted with MTBE and neutralised using dil. hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1). The further purification is carried out by recrystallisation from n-heptane, giving 1-ethoxy-2,3-difluoro-4-(4-propylcyclohexylethynyl)benzene as a colourless solid (m.p. 64° C.). This has the phase sequence: C 64° C. I. The properties, extrapolated from a 10% solution in ZLI-4792, are:

후처리

  1. temperatureAfter cooling
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with sodium chloride solution
  5. customdried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, n-heptane:chlorobutane=9:1)
  8. customThe further purification
  9. customis carried out by recrystallisation from n-heptane

출처 및 근거

ORD 기록
ord-e76b039464e14f3dad843f034d8cb177
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08945420B2

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