Pentafluoroiodobenzene → 2,3,4,5,6-Pentafluoro-2'-methoxy-5'-methyl-1,1'-biphenyl

HRID 1847102

反応式

HRID 1847102 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1B1OC(C)(C)C(C)(C)O1.I[C:20]1[C:25]([F:26])=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:21]=1[F:30]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[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:26][C:25]1[C:24]([F:27])=[C:23]([F:28])[C:22]([F:29])=[C:21]([F:30])[C:20]=1[C:4]1[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

7

反応物 2

HCID 70008PentafluoroiodobenzeneHCID 796621212-(2-Methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 573278032,3,4,5,6-Pentafluoro-2'-methoxy-5'-methyl-1,1'-biphenyl収率 93%

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 11430Potassium Carbonate溶媒

実験手順

Compound 5 (11.3 g, 45.54 mmol, 1 equiv) and iodopentafluorobenzene (10.6 g, 36.2 mmol, 1 equiv) were dissolved in toluene (200 mL) and 1.0M potassium carbonate solution (200 mL). Tetrabutylammonium bromide (1.6 g, 5 mmol, 0.11 equiv) was added and the solution sparged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (2.63 g, 2.28 mmol, 0.05 equiv) was added and the reaction was refluxed for one day. The reaction was cooled to room temperature, then the layers were separated. The aqueous phase was back extracted with ethyl acetate (2×200 mL). Combined organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over silica gel (200 g), eluting with heptanes to give 2,3,4,5,6-pentafluoro-2′-methoxy-5′-methyl-1,1′-biphenyl (6) (9.7 g, 74% yield) as a pale-yellow oil. This material contained a small amount of unreacted iodopentafluorobenzene which was identified by 19F NMR. The material was used subsequently.

後処理

  1. customthe solution sparged with nitrogen for 10 minutes
  2. temperaturethe reaction was refluxed for one day
  3. customthe layers were separated
  4. extractionThe aqueous phase was back extracted with ethyl acetate (2×200 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (200 g)
  8. washeluting with heptanes

出典と根拠

ORDレコード
ord-e95ef93340a349c391c502c27ec4471d
出典データセット
uspto-grants-2015_02
特許番号
US08952114B2

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