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

HRID 1057454Notes

Reaction equation

HRID 1057454 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)[CH3:2].Br[C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=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:23][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[CH:19][C:18]=1[N+:20]([O-:22])=[O:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 27739203-Ethoxybenzeneboronic acid

Product 1

HCID 105633474-Fluoro-3'-ethoxy-3-nitrobiphenylYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of 4.2 g of 3-ethoxyphenylboronic acid, 5.0 g of 5-bromo-2-fluoronitrobenzene and 22 mL of 2 M sodium carbonate solution in 50 mL of toluene and 50 mL of ethanol. The mixture was heated to refulux for 2 hours, concentrated, water was added and the mixture was extracted twice with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried and concentrated. The residue was chromatographed on silica gel in 5% ethyl acetate in hexane to give 5.3 g (90% yield) of crude 4-fluoro-3′-ethoxy-3-nitrobiphenyl as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. concentrationconcentrated
  3. additionwater was added
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe ethyl acetate layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel in 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c3126dada51c4c488c7ba2b20d5226f9
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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