Toluene → 4'-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester

HRID 1677133ノート

反応式

HRID 1677133 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C([O-])([O-])=[O:26].[K+].[K+].C1(C)C=CC=CC=1>CCO>[CH3:12][O:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH:9]3[CH2:11][CH2:10]3)=[O:26])=[CH:4][CH:3]=2)=[CH:20][CH:21]=1)=[O:15]

参加物

6

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 116513971-Bromo-4-(cyclopropylmethyl)benzene

生成物 1

HCID 579800374'-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Procedure I′: 1.8 g of (4-bromophenyl)cyclopropylmethane (8.0 mmol), 1.80 g of (4-methoxycarbonylphenyl)boronic acid (10.0 mmol) are put into flask with 8.0 ml of aqueous 2M K2CO3 and 90 ml of toluene:EtOH=20:1. The mixture is deoxygenated and stirred at room temperature under N2 for 30 min. 280 mg of tetrakis(triphenylphosphine)-palladium is added. The reaction mixture is stirred under reflux for overnight. Organic layer is separated from water layer and water layer is extracted with CH2Cl2. All organic layers are combined together and dried over Na2SO4 and evaporated. The crude product is applied to silica-gel column chromatography (Hexane:AcOEt=8:1→3:1). 4′-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester is recrystallized from hexane/AcOEt (849 mg, 38%). Mass spectrum (m/e): 214 (M+1)

後処理

  1. customThe mixture is deoxygenated
  2. addition280 mg of tetrakis(triphenylphosphine)-palladium is added
  3. stirringThe reaction mixture is stirred
  4. temperatureunder reflux for overnight
  5. customOrganic layer is separated from water layer and water layer
  6. extractionis extracted with CH2Cl2
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. custom4′-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester is recrystallized from hexane/AcOEt (849 mg, 38%)

出典と根拠

ORDレコード
ord-5a468eb09b044df580aa1cdb123328b5
出典データセット
uspto-grants-2011_08
特許番号
US08008301B2

反応ノート

読み込み中…