Ethanol → Ethyl 2',4'-dimethyl[1,1'-biphenyl]-3-carboxylate

HRID 273377

반응식

HRID 273377 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)C>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.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:21]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10796Cesium carbonateHCID 90488Ethyl 3-bromobenzoateHCID 4198739(2,4-Dimethylphenyl)boronic acid

생성물 1

HCID 23111852Ethyl 2',4'-dimethyl[1,1'-biphenyl]-3-carboxylate수율 104.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

(2,4-Dimethylphenyl)boronic acid (3.0 g, 20.0 mmol), ethyl 3-bromobenzoate (4.3 g, 18.8 mmol) and cesium carbonate (9.8 g, 30.0 mmol) were added to a mixture of ethanol (20 mL) and toluene (80 mL), and after argon substitution, tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 70° C. for 18 hrs. The reaction mixture was cooled and insoluble material was filtered off through celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to give the title compound (5.0 g, yield 100%) as a colorless oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationinsoluble material was filtered off through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)

출처 및 근거

ORD 기록
ord-a82fda5bbb3f4b1b9fdea821085eb06c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456218B2

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