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

HRID 1847100

反応式

HRID 1847100 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9428941c0fc94688951be6ebf416a85b
出典データセット
uspto-grants-2015_02
特許番号
US08952114B2

関連ノート

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