Potassium Carbonate → 2,3,4,5,5',6-Hexafluoro-2'-methoxy-1,1'-biphenyl

HRID 1847100

반응식

HRID 1847100 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.I[C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[F:24].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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>[F:20][C:19]1[C:18]([F:21])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:11][CH3:12]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 70008PentafluoroiodobenzeneHCID 27826735-Fluoro-2-methoxyphenylboronic acid

생성물 1

HCID 867104532,3,4,5,5',6-Hexafluoro-2'-methoxy-1,1'-biphenyl수율 277.5%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

Compound 1 (6.3 g, 3.7 mmol, 1 equiv) and iodopentafluorobenzene (5.5 mL, 4 mmol, 1.2 equiv) were dissolved in toluene (120 mL). 1.0 M Potassium carbonate solution (120 mL), tetrabutylammonium bromide (600 mg), and tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol, 0.05 equiv) were added. Nitrogen was sparged through the mixture for 10 minutes. The reaction was refluxed 18 hours, then cooled to room temperature. The layers were separated and the aqueous layer was extracted with methyl tert-butyl ether (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over silica gel (100 g), eluting with a gradient of 0 to 4% ethyl acetate in heptane to give 2,3,4,5,5′,6-hexafluoro-2′-methoxy-1,1′-biphenyl (2) (3.0 g, 28% yield) as an off-white solid.

후처리

  1. customNitrogen was sparged through the mixture for 10 minutes
  2. temperatureThe reaction was refluxed 18 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methyl tert-butyl ether (2×50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (100 g)
  8. washeluting with a gradient of 0 to 4% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-9428941c0fc94688951be6ebf416a85b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952114B2

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