Toluene → 4-Fluoro-3'-methoxy-3-nitrobiphenyl

HRID 11536

Reaction equation

HRID 11536 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>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.C(O)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([O:13][CH3:12])[CH:19]=2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 104907024-Fluoro-3'-methoxy-3-nitrobiphenyl

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

4-Bromo-1-fluoro-2-nitro-benzene (5 gms.), 3.85 gms. 3-methoxyphenylboronic acid and 22 mL of a 2M aqueous solution of sodium carbonate are suspended in 100 mL of a 1:1 (v:v) mix of toluene and ethanol. The resulting suspension is then treated with 0.8 gms. tetrakis(triphenylphosphine)palladium(0) at room temperature. The reaction mixture is then heated at reflux for 12 h. The reaction mixture is subsequently concentrated in vacuo, and the resulting residue is taken up in ethyl acetate (200 mL). The ethyl acetate solution is then washed successively with water (2×200 mL), and brine (2×200mL). The organic layer is then dried by filtering through phase separator paper and concentrated in vacuo to yield 7.19 gms. of crude product. The crude product is then recrystallized from hot ethanol yielding 4-fluoro-3′-methoxy-3-nitro-biphenyl as a yellow-white solid in the amount of 4.767 gms.

Workup

  1. additionThe resulting suspension is then treated with 0.8 gms
  2. customat room temperature
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for 12 h
  5. concentrationThe reaction mixture is subsequently concentrated in vacuo
  6. washThe ethyl acetate solution is then washed successively with water (2×200 mL), and brine (2×200mL)
  7. customThe organic layer is then dried
  8. filtrationby filtering through phase
  9. concentrationconcentrated in vacuo
  10. customto yield 7.19 gms
  11. customThe crude product is then recrystallized from hot ethanol

Sources & evidence

ORD record
ord-842c8a1fc9d040ed9e1571297c6d1a76
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Linked notes

Loading…