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

HRID 1937581Notes

Reaction equation

HRID 1937581 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 100.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0.7 g) was added to a mixture of 5 g of 3-methoxyphenylboronic acid, 3.8 g 5-bromo-2-fluoronitrobenzene and 11 mL 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 then brine, dried, and concentrated to give an oily solid. The solid was chromatographed on silica gel using 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
  4. dry with materialbrine, dried
  5. concentrationconcentrated
  6. customto give an oily solid
  7. customThe solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-2a7f49aaf103407189cce1798056cb8c
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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