Potassium Carbonate → 2'-Methyl[biphenyl]-2-amine

HRID 338199Notes

Reaction equation

HRID 338199 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[NH2:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 119922-BromoanilineHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 12072412'-Methyl[biphenyl]-2-amineYield 84.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Added together 2-methylphenyl boronic acid (24.7 g, 181 mmol), 2-bromo aniline (25.7 g, 151 mmol), palladium(II)acetate (0.85 g, 3.78 mmol), triphenylphosphine (4.0 g, 15.1 mmol), a 2 M solution of potassium carbonate (204 mL) and ethylene glycol dimethyl ether (223 mL) and heated the reaction mixture at reflux for 18 hours. After the reaction was cooled to room temperature, the aqueous phase was separated from the organic phase. The aqueous phase was extracted with ethyl acetate and the organic extractions were combined, dried over magnesium sulfate and filtered. The crude product was purified by silica gel column chromatography using 10% ethyl acetate in hexanes as the eluants. The pure fractions were collected, combined and concentrated to give 2-amino-2′-methyl-biphenyl (23.5 g, 84.8% yield) whose structure was confirmed by GCMS and NMR.

Workup

  1. temperatureat reflux for 18 hours
  2. customthe aqueous phase was separated from the organic phase
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. extractionthe organic extractions
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe crude product was purified by silica gel column chromatography
  8. customThe pure fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ab31a067ccf04686bf52563531b0dcfa
Source dataset
uspto-grants-2014_11
Patent number
US08889864B2

Reaction notes

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