Sodium Carbonate → 4-Fluoro-3-nitro-1,1'-biphenyl

HRID 24461

Reaction equation

HRID 24461 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[CH:13][C:14]([F:20])=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=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:20][C:14]1[CH:13]=[CH:12][C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][C:15]=1[N+:17]([O-:19])=[O:18]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 106802714-Fluoro-3-nitro-1,1'-biphenylYield 96.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of 3.1 g of benzeneboronic acid, 5 g of 5-bromo-2-fluoronitrobenzene and 22 ml of 2M aqueous sodium carbonate 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 yellow oil. The oil was chromatographed on silica gel (5% ethyl acetate in hexane) to give 4.75 g (96%) of 4-fluoro-3-nitrobiphenyl as a yellow oil.

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 yellow oil
  8. customThe oil was chromatographed on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b7a8031b8fb841babd8687ddafd9ec36
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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