Sodium Carbonate → 4'-Chloro-4-ethyl-3-nitrobiphenyl

HRID 72250Notes

Reaction equation

HRID 72250 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 75669964-Bromo-1-ethyl-2-nitrobenzene

Product 1

HCID 594459324'-Chloro-4-ethyl-3-nitrobiphenylYield 104.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

To 4-bromo-1-ethyl-2-nitrobenzene (20.0 g, 0.087 mol) in 150 ml 1,2-dimethoxyethane is added, at room temperature, 4-chlorophenylboronic acid (14.98 g, 0.096 mol) and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 0.00174 mol) and nitrogen gas is bubbled through the mixture. After stirring for 10 minutes at 20° C., a solution of sodium carbonate (73.8 g, 0.696 mol) in water (350 ml) is added and mixture is heated at reflux for 16 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth, washing with 200 ml of ethyl acetate. The mixture is poured into a separating funnel and the two phases are separated. The aqueous phase is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to give 4′-chloro-4-ethyl-3-nitrobiphenyl (23.84 g) as a brown oil used without further purification in the next step.

Workup

  1. temperaturemixture is heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through diatomaceous earth
  5. washwashing with 200 ml of ethyl acetate
  6. additionThe mixture is poured into a separating funnel
  7. customthe two phases are separated
  8. extractionThe aqueous phase is extracted with ethyl acetate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-de6c0b27856847908ccfaf39d9550de5
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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