4-Bromotoluene → 4'-Methyl-biphenyl-3-carboxylic acid ethyl ester

HRID 22246

반응식

HRID 22246 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.I[C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([C:20]2[CH:30]=[CH:29][CH:28]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=2)=[CH:4][CH:5]=1

참가 물질

7

반응물 4

HCID 78054-BromotolueneHCID 14487Diisobutylaluminum hydrideHCID 143542Ethyl 3-iodobenzoateHCID 5462224Magnesium2회

생성물 1

HCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester수율 59.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Magnesium (1.6 g) and p-bromotoluene (10.26 g) in 60 ml of tetrahydrofuran were stirred and warmed until the reaction commenced. When the exothermic reaction had finished, the mixture was refluxed overnight. In a separate flask, 4 ml of DIBAL (1M in toluene) was added to a suspension of bis(triphenylphosphine)palladium(II) chloride (1.4 g) in 100 ml of tetrahydrofuran, followed by ethyl 3-iodobenzoate (11.04 g). To this mixture, the magnesium reagent prepared above was added dropwise, causing an exothermic reaction. The reaction mixture was stirred overnight at room temperature, and then quenched by addition of dilute hydrochloric acid. The mixture was extracted with ether, and the organic layer washed with water, and then saturated brine. The organic layer was separated, dried over sodium sulfate, the solvent evaporated under reduced pressure, and the residue chromatographed on silica gel, eluting with 5% ethyl acetate in heptane, to yield 5.69 g of ethyl 4'-methylbiphenyl-3-carboxylate, a compound of Formula (17), as a pale yellow oil.

후처리

  1. temperaturewarmed until the reaction commenced
  2. customWhen the exothermic reaction
  3. temperaturethe mixture was refluxed overnight
  4. additionabove was added dropwise
  5. customan exothermic reaction
  6. customquenched by addition of dilute hydrochloric acid
  7. extractionThe mixture was extracted with ether
  8. washthe organic layer washed with water
  9. customThe organic layer was separated
  10. dry with materialdried over sodium sulfate
  11. customthe solvent evaporated under reduced pressure
  12. customthe residue chromatographed on silica gel
  13. washeluting with 5% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-8ade3edc649f4a38a227428b6258ced6
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428037

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