Sodium Carbonate → 4-Fluoro-4'-methoxy-3-nitrobiphenyl

HRID 1840807Notes

Reaction equation

HRID 1840807 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:16]1[CH:15]=[CH:14][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 107529914-Fluoro-4'-methoxy-3-nitrobiphenyl

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (I g) was added to a mixture of 5 g of 4methoxyphenylboronic acid, 6.6 g of 5-bromo-2-fluoronitrobenzene and 30 mL of 2 M sodium carbonate solution in 50 mL of toluene and 50 mL of ethanol. The mixture was refluxed for 2 hours, concentrated, and the residue extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried, and concentrated to give a brown oily solid. The solid was chromatographed on silica gel (5% ethyl acetate in hexane) to give crude 4-fluoro-4′-methoxy-3-nitrobiphenyl as a pale yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated
  3. extractionthe residue extracted twice with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a brown oily solid
  8. customThe solid was chromatographed on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c445e77d00044ee9ae794f48ae11487a
Source dataset
uspto-grants-2004_01
Patent number
US06683082B2

Reaction notes

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