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

HRID 10070

반응식

HRID 10070 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) Dichloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ae0c0d393cb48bfbc9062688fae2658
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091380B2

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