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

HRID 1700234Notes

Reaction equation

HRID 1700234 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 refluxed for 2 hours, concentrated, water was added and the mixture was extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and brine, then dried, and concentrated. The residue was chromatographed on silica gel (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 ethyl acetate layer was washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-07f92d8ef1d34ef5b9f99d725f6883e8
Source dataset
uspto-grants-2002_02
Patent number
US06350754B2

Reaction notes

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