Toluene → 4-Ethoxy-3,3'-difluoro-4'-((4-propylcyclohexyl)methoxy)-[1,1'-biphenyl]-2,2'-dicarboaldehyde

HRID 718489ノート

反応式

HRID 718489 の反応式
Br[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[C:27]([CH:34]=[O:35])[C:26]=1[F:36])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].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.O.C(O)C>[CH2:22]([O:24][C:25]1[C:26]([F:36])=[C:27]([CH:34]=[O:35])[C:28]([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)=[CH:4][CH:3]=2)=[CH:29][CH:30]=1)[CH3:23]

参加物

9

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 469186104-Ethoxy-3-fluoro-2-formylphenylboronic acidHCID 866960666-Bromo-2-fluoro-3-((4-propylcyclohexyl)methoxy)benzaldehyde

生成物 1

HCID 866960654-Ethoxy-3,3'-difluoro-4'-((4-propylcyclohexyl)methoxy)-[1,1'-biphenyl]-2,2'-dicarboaldehyde収率 80.3%

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Under a nitrogen atmosphere, a mixture of compound (62) (4.20 g, 11.76 mmol), compound (55) (2.74 g, 12.93 mmol) prepared in Example 1, tetrakis(triphenylphosphine)palladium (0.14 g, 0.121 mmol), potassium carbonate (3.25 g, 23.51 mmol) and TBAB (0.76 g, 2.351 mmol) was refluxed in a toluene (20 mL)-ethanol (10 mL)-water (50 mL) solvent for 5 hours. The reaction mixture was extracted with 20 mL of toluene three times, combined organic layers were washed with water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-ethoxy-3,3′-difluoro-4′-((4-propylcyclohexyl)methoxy)-[1,1′-biphenyl]-2,2′-dicarboaldehyde (63) (4.20 g, yield 80.3%) was obtained.

後処理

  1. extractionThe reaction mixture was extracted with 20 mL of toluene three times
  2. washwere washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. distillationa solvent was distilled off by an evaporator
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d5be42ece89d433a845addaef5a9d56a
出典データセット
uspto-grants-2015_11
特許番号
US09193908B2

反応ノート

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