Sodium Carbonate → HCID 59450506, compound

HRID 72300Notes

Reaction equation

HRID 72300 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(OCC)(=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:8][C:6]1[CH:5]=[CH:4][C:3]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)=[C:2]([F:1])[CH:7]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 4193595(4-Chloro-2-fluorophenyl)boronic acidHCID 75669964-Bromo-1-ethyl-2-nitrobenzene

Product 1

HCID 59450506HCID 59450506, compoundYield 98.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) is added to a solution of 2-fluoro-4-chlorophenylboronic acid (1.25 g, 7.17 mmol) and 4-bromo-1-ethyl-2-nitrobenzene (1.50 g, 6.52 mmol) in 1,2-dimethoxyethane (12 ml) and the mixture is stirred at room temperature for 15 minutes. A solution of sodium carbonate (5.52 g, 52 mmol) in water (26 ml) is added and the mixture is heated to reflux for 17 hours. The reaction mixture is cooled to room temperature, diluted with ethyl acetate and the two phases separated. The organic phase is collected, the aqueous phase is extracted with ethyl acetate and the organic solutions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 4′-chloro-4-ethyl-2′-fluoro-3-nitrobiphenyl (1.795 g), used without further purification in the next step.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 17 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe two phases separated
  5. customThe organic phase is collected
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-614993ffde28407cb8fb564fd5ea12dd
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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