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

HRID 1790985Notes

Reaction equation

HRID 1790985 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 (0.7 g) was added to a mixture of 3.8 g of 3-methoxyphenylboronic acid, 5 g of 5-bromo-2-fluoronitrobenzene and 11 mL of 2 M sodium carbonate solution in 100 mL of toluene. The mixture was heated to reflux for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate, brine, dried, and concentrated to give an oily solid. The solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6 to give 4.3 g (77% yield) of 4-fluoro-3′-methoxy-3-nitrobiphenyl.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with saturated sodium bicarbonate, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give an oily solid
  8. customThe solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6

Sources & evidence

ORD record
ord-0aedcfaa8c0a46d5b70cbff208230660
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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