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

HRID 49123Notes

Reaction equation

HRID 49123 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 benzeneboronic acid (3.1 g), 5-bromo-2-fluoronitrobenzene (5 g) and 22 mL of 2M sodium carbonate solution in toluene (50 mL) and ethanol (50 mL). The mixture was heated to reflux for 2 hours, concentrated, and the residue was extracted twice with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried, and concentrated to give a yellow oil. The oil was purified by column chromatography on silica gel in 5% ethyl acetate in hexane to give 4.75 g (96% yield) of 4-fluoro-3-nitrobiphenyl as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. extractionthe residue was extracted twice with ethyl acetate
  5. washThe ethyl acetate layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThe oil was purified by column chromatography on silica gel in 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fa8ace79f317475eb2bc5df0b6e69397
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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