Sodium Carbonate → 4'-Chloro-2-nitro-1,1'-biphenyl

HRID 1791114Notes

Reaction equation

HRID 1791114 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.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>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 113411-Bromo-2-nitrobenzeneHCID 742994-Chlorophenylboronic acid

Product 1

HCID 2355494'-Chloro-2-nitro-1,1'-biphenylYield 86.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromonitrobenzene (646 mg) in THF (17 ml) under nitrogen was added tetrakis(triphenylphosphine)palladium (0) (900 mg). The resulting mixture was stirred at room temperature for 20 min, then a solution of 4-chlorophenylboronic acid (1.0 g) in ethanol (17 ml) was added and the resulting mixture stirred at room temperature for 1 hr. 2M sodium carbonate (17 ml) was then added and the reaction heated to reflux for 2 hrs. The mixture was then allowed to cool and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and the aqueous layer removed. The organic phase was washed with brine (20 ml), dried (magnesium sulfate), filtered and concentrated. The reside was purified by flash chromatography (0–10% ethyl acetate/hexane) to afford the sub-title compound as a yellow solid (646 mg): 1H NMR (400 MHz, CDCl3) δ 7.24–7.31 (2H, m), 7.41–7.47 (3H, m), 7.52 (1H, m), 7.65 (1H, m), 7.90 (1H, d).

Workup

  1. stirringthe resulting mixture stirred at room temperature for 1 hr
  2. temperaturethe reaction heated
  3. temperatureto reflux for 2 hrs
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  7. customthe aqueous layer removed
  8. washThe organic phase was washed with brine (20 ml)
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe reside was purified by flash chromatography (0–10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-edf9fdfcefd14954ae03271d59898a8b
Source dataset
uspto-grants-2006_07
Patent number
US07074782B2

Reaction notes

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