Potassium Carbonate → HCID 58241683, compound

HRID 2191199Notes

Reaction equation

HRID 2191199 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(#N)C.O.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]>[CH3:9][O:8][C:7]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=[C:3]([O:13][CH3:14])[C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 58241680HCID 58241680, compound

Product 1

HCID 58241683HCID 58241683, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 67448433Dioxane acetonitrile waterSolvent

Conditions

Temperature
90 °C

Procedure

2-Iodo-1,3-dimethoxy-4-nitrobenzene (0.5 g, 1.62 mmol) was dissolved in dioxane/acetonitrile/water (10 ml/2 ml/2 ml), and 2-tolylboronic acid was added. Pd(dppf)Cl2 (0.11 mg, 0.16 mmol) and K2CO3 (0.33 g, 2.43 mmol) were added to this, and the mixture was stirred at 90° C. for 32 h. After concentration, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate. This gave 2,6-dimethoxy-2′-methyl-3-nitrobiphenyl (0.2 g) as a colorless powder.

Workup

  1. concentrationAfter concentration
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-64f5b2fc1cc1464b8dda7a9fde4b2068
Source dataset
uspto-grants-2012_12
Patent number
US08329619B2

Reaction notes

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