Water → Methyl 4'-Cyano[1,1'-biphenyl]-2-carboxylate

HRID 10070

反応式

HRID 10070 の反応式
O.C(=O)([O-])[O-].[K+].[K+].I[C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)#[N:20]>[Pd](Cl)Cl.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C1COCC1>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:9]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:23][CH:22]=1)#[N:20]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 27343264-Cyanophenylboronic acid

生成物 1

HCID 21988942Methyl 4'-Cyano[1,1'-biphenyl]-2-carboxylate収率 86%

試薬・触媒・溶媒 2

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) Dichloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 500 mL of THF was added water (18.4 mL, 1.02 mol), potassium carbonate (70.5 g, 0.510 mol), methyl 2-iodobenzoate (53.5 g, 0.204 mol), 4-cyano-phenylboronic acid (30.0 g, 0.204 mol) and bis-(tri-o-tolylphosphine) palladium (II) chloride (1.65 g, 2.04 mmol). This mixture was heated to reflux for 3.5 hours and then cooled to ambient temperature for continued stirring overnight. The solvent was then removed under reduced pressure prior to dilution with EtOAc/water. The organic layer was extracted with additional EtOAc. The combined organics were washed with water, then brine. The organics were then dried over sodium sulfate, filtered, and then concentrated to obtain the crude product. This crude product was passed through a silica pad, eluting with 8:1 heptane:EtOAc to get 41.6 grams of methyl 4′-cyano-1,1′-biphenyl-2-carboxylate.

後処理

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customThe solvent was then removed under reduced pressure
  4. extractionThe organic layer was extracted with additional EtOAc
  5. washThe combined organics were washed with water
  6. dry with materialThe organics were then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain the crude product
  10. washeluting with 8:1 heptane

出典と根拠

ORDレコード
ord-5ae0c0d393cb48bfbc9062688fae2658
出典データセット
uspto-grants-2006_08
特許番号
US07091380B2

関連ノート

読み込み中…