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

HRID 366581

Reaction equation

HRID 366581 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.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:22][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 104907024-Fluoro-3'-methoxy-3-nitrobiphenylYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of 5 g 3-methoxyphenylboronic acid, 5 g 5-bromo-2-fluoronitrobenzene and 11 mL of 2 M sodium carbonate solution in 100 mL of toluene. The mixture was refluxed for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate and brine and then dried and concentrated to give an oily solid. The solid was chromatographed on silica gel (ethyl acetate:hexane (1:6)) to give 4.3 g (77% yield) of 4-fluoro-3'-methoxy-3- nitrobiphenyl.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with saturated sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oily solid
  7. customThe solid was chromatographed on silica gel (ethyl acetate:hexane (1:6))

Sources & evidence

ORD record
ord-30e6b08d25734c5a8305b30adc772df7
Source dataset
uspto-grants-2000_10
Patent number
US06130238

Linked notes

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