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

HRID 1937589Notes

Reaction equation

HRID 1937589 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 5-bromo-2-fluoronitrobenzene and 22 mL 2 M sodium carbonate solution in 50 mL toluene and 50 mL ethanol. The mixture was refluxed for 2 hours and then concentrated. Water was added and the mixture was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water and brine brine, then dried and concentrated. The residue was chromatographed on silica gel using 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 refluxed for 2 hours
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and brine brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel using 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-79b9fb8c993a49319f450396ddc10800
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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