Potassium Carbonate → N-(4'-chloro-3-ethylbiphen-4-yl)acetamide

HRID 341684Notes

Reaction equation

HRID 341684 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH2:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 2735223N-(4-bromo-2-ethylphenyl)acetamide

Product 1

HCID 59450487N-(4'-chloro-3-ethylbiphen-4-yl)acetamideYield 91.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of N-(4-bromo-2-ethylphenyl)acetamide (20 g, 0.082 mol) in toluene (1200 ml) and ethanol (400 ml), 4-chlorobenzene boronic acid (15.5 g, 0.099 mol) is added under an atmosphere of nitrogen, and the reaction mixture is heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.0 g, 0.0017 mol) is added followed by 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is refluxed for 4 hours then cooled to room temperature. The reaction mass is filtered through diatomaceous earth, and the filtrate is evaporated under reduced pressure. The residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (3×500 ml) and the organic solutions are combined and concentrated under reduced pressure to give N-(4′-chloro-3-ethylbiphen-4-yl)acetamide (20.5 g).

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. temperaturethen cooled to room temperature
  3. filtrationThe reaction mass is filtered through diatomaceous earth
  4. customthe filtrate is evaporated under reduced pressure
  5. customThe residue is partitioned between ethyl acetate and water
  6. extractionThe aqueous phase is extracted with ethyl acetate (3×500 ml)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5388bc0b48604eeaa7b66a6db5dc15f4
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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