Toluene → 4-Ethoxy-3,3'-difluoro-4'-propyl-[1,1'-biphenyl]-2,2'-dicarboaldehyde

HRID 718485ノート

反応式

HRID 718485 の反応式
Br[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([CH:26]=[O:27])[C:18]=1[F:28])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+].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>[CH2:14]([O:16][C:17]1[C:18]([F:28])=[C:19]([CH:26]=[O:27])[C:20]([C:2]2[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1)[CH3:15]

参加物

9

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 469186104-Ethoxy-3-fluoro-2-formylphenylboronic acidHCID 866960636-Bromo-2-fluoro-3-propylbenzaldehyde

生成物 1

HCID 866960644-Ethoxy-3,3'-difluoro-4'-propyl-[1,1'-biphenyl]-2,2'-dicarboaldehyde収率 80.5%

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 (51) (4.9 g, 19.99 mmol), compound (55) (4.9 g, 23.12 mmol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.199 mmol), sodium carbonate (4.9 g, 46.23 mmol) and TBAB (0.96 g, 2.978 mmol) was refluxed in a toluene (30 mL)-ethanol (20 mL)-water (50 mL) solvent for 5 hours. The reaction mixture was extracted with 30 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, 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′-propyl-[1,1′-biphenyl]-2,2′-dicarboaldehyde (56) (5.35 g, yield 80.5%) was obtained.

後処理

  1. extractionThe reaction mixture was extracted with 30 mL of toluene three times
  2. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, 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-d0c9df6c7a18490ebe6a944bceb474b1
出典データセット
uspto-grants-2015_11
特許番号
US09193908B2

反応ノート

読み込み中…