Sodium Carbonate → 2-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrile

HRID 1178472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178472
Br[C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH:21]=[O:22].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]([C:3]1[CH:4]=[C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH:19]=[CH:20][C:2]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 219303662-(4-Bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

Produkt 1

HCID 219303872-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrileAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-(4-bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (1.76 g, 4.76 mmol) and Pd(dba)3 (21.8 mg, 5 mole %) in dimethoxyethane (15 ml) was added a solution of phenylboronic acid (609 mg, 5 mmol), triphenylphosphine (15 mg, 12 mole %) and sodium carbonate (530 mg, 5 mmol) in water (10 ml). The mixture was refluxed for 3 h. The solvent was evaporated off and the aqueous layer was extracted with dichloromethane. The extracts were dried with MgSO4 and filtered through silica. Evaporation yielded a brown solid (1.73 g, 99%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated off
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe extracts were dried with MgSO4
  5. filtrationfiltered through silica
  6. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-f4f4e5cd517849939e86d6783a9a570a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276528B2

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