Dichloromethane → Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

HRID 403859

Reaktionsgleichung

Reaktionsgleichung von HRID 403859
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:12][C:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 22031226Methyl 4-bromo-2-methylbenzoate

Produkt 1

HCID 59385226Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
82.5 °C

Versuchsvorschrift

The compound of example 219 (10 g, 0.044 mol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (13.16 gm, 0.0528 mole) and Pd(dppf)Cl2:CH2Cl2 (1.07 g, 0.00132 mol) were taken in DMF (250 mL) under an argon atmosphere. To this reaction mixture, degassed 2M solution of Na2CO3 (14 g, 0.132 mol, 66.5 mL) was added. The reaction mixture was stirred at 80-85° C. for 1 to 1.5 h. After completion of the reaction, water was added and the product obtained was extracted with ether. The combined ether layer was washed with brine and dried over anhydrous Na2SO4 or MgSO4. The solvent was evaporated and the product was purified by column (silica gel, 20% ethyl acetate in petroleum ether) to obtain the title compound.

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. customthe product obtained
  4. extractionwas extracted with ether
  5. washThe combined ether layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4 or MgSO4
  7. customThe solvent was evaporated
  8. customthe product was purified by column (silica gel, 20% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-f22d68aecef143089cc2c8ab56492826
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748426B2

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