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

HRID 54197

反応式

HRID 54197 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45bccc0fd90f4902bf29bd9f65b6b1e9
出典データセット
uspto-grants-1997_04
特許番号
US05622937

関連ノート

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