Sodium Carbonate → [1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl ester

HRID 54197

반응식

HRID 54197 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.[Cl-].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 27339582-Methoxyphenylboronic acidHCID 86643102Sodium chloride ethyl acetate

생성물 1

HCID 5152372[1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl ester수율 64%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매2회

실험 절차

Methyl 3-bromobenzoate (1.99 g, 9.25 mmol), tetrakis(triphenylphosphine) palladium(O) (110 mg), sodium carbonate (2.04 g, 19 mmol in 5 ml water) and toluene (10 ml) were degassed under nitrogen in a 25 ml flask fitted with a reflux condenser. 2-Methoxybenzeneboronic acid (1.46 g, 9.61 mmol) in toluene (1 ml) was added and the mixture was heated at reflux for two days then mixed with 1:1 saturated sodium chloride/ethyl acetate (15 ml). The organic materials were separated, dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient hexane to 8:1 hexane/ethyl acetate) which gave methyl 3-(2-methoxyphenyl)benzoate (1.43 g, 64%), m.p.: 92°-93° C.

후처리

  1. customfitted with a reflux condenser
  2. temperaturethe mixture was heated
  3. temperatureat reflux for two days
  4. customThe organic materials were separated
  5. dry with materialdried (MgSO4)
  6. concentrationthen concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (SiO2, gradient hexane to 8:1 hexane/ethyl acetate) which

출처 및 근거

ORD 기록
ord-45bccc0fd90f4902bf29bd9f65b6b1e9
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622937

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