Sodium Carbonate → Ethyl 3'-methoxy[1,1'-biphenyl]-2-carboxylate

HRID 278165

반응식

HRID 278165 반응식
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[Na+].[Na+].[CH3:19][O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>COCCOC.O.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>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 80186Ethyl 2-bromobenzoateHCID 2734370(3-Methoxyphenyl)boronic acid

생성물 1

HCID 22627113Ethyl 3'-methoxy[1,1'-biphenyl]-2-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
100 °C

실험 절차

To a stirred solution of ethyl 2-bromobenzoate (13.7 g, 59.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.46 g, 3.0 mmol) in 1,2-dimethoxyethane (600 mL) was added 2 M aq. Na2CO3 (60 mL, deoxygenated). 3-Methoxyphenylboronic acid (10.0 g, 65.8 mmol) was added in 1,2-dimethoxyethane (80 mL) and the mixture was heated to 100° C. for 36 hours, under argon atmosphere. The mixture was cooled, diluted with water (1 L) and extracted with EtOAc (2×800 mL). The combined organic extracts were washed with sat. aq. NaHCO3, then brine, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with a gradient of 0-10% EtOAc in hexane, to give the titled product as a colorless oil.

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (2×800 mL)
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3
  4. dry with materialbrine, then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with a gradient of 0-10% EtOAc in hexane

출처 및 근거

ORD 기록
ord-14c522aeffb34f50a4034657d167f1c8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358985B1

연결된 노트

불러오는 중…