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

HRID 718485노트

반응식

HRID 718485 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0c9df6c7a18490ebe6a944bceb474b1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193908B2

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