Sodium Carbonate → 5-(4-Chlorophenyl)-2-ethylaniline

HRID 1027380Notes

Reaction equation

HRID 1027380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:13]=[CH:14][C:15]([CH2:19][CH3:20])=[C:16]([CH:18]=1)[NH2:17].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([CH2:19][CH3:20])=[C:16]([CH:18]=2)[NH2:17])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 233467565-Bromo-2-ethylaniline

Product 1

HCID 594459455-(4-Chlorophenyl)-2-ethylanilineYield 88.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

4-Chlorophenylboronic acid (13.2 g, 0.08 mol) and tetrakis(triphenylphosphine) palladium (0) (2.4 g, 0.002 mol) are added to a solution of 5-bromo-2-ethylaniline (14.1 g, 0.07 mol) in 1,2-dimethoxyethane (140 ml). After stirring the reaction mixture for 15 minutes at 20° C., a solution of 20% aqueous sodium carbonate (300 ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexane to give 5-(4-chlorophenyl)-2-ethylaniline (14.3 g).

Workup

  1. temperaturethe resulting mixture is refluxed for 24 hours
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted
  4. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo
  7. customThe residue is further purified by column chromatography on silica gel
  8. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6b3156a4c4b740618952bde6983f1972
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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