Hydrochloric Acid → N-(2'-Chloro-6'-methyl-phenyl)-4-ethylaniline

HRID 603338Notes

Reaction equation

HRID 603338 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[CH2:10]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)[CH3:11].CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:15]1[CH:16]=[CH:17][C:12]([CH2:10][CH3:11])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 68972-Chloro-6-methylanilineHCID 153131-Bromo-4-ethylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 57952157N-(2'-Chloro-6'-methyl-phenyl)-4-ethylanilineYield 58.4%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5.2 g (37 mmol) of 2-chloro-6-methylaniline and 6.95 g (37.6 mmol) of 4-ethyl bromobenzene in 50 ml of toluene is added 6.5 g (68 mmol) sodium tert-butoxide, 180 mg (0.89 mmol) tri-tert-butylphosphine (dissolved in 2 ml of toluene) and 300 mg (0.52 mmol) of bis-dibenzylideneacetone palladium(0). The mixture is heated under nitrogen to 90° C. for 3 hours and then cooled to room temperature. Hyflo (1 g), water (30 ml) and cone, hydrochloric acid (10 ml) are added and after stirring for 30 minutes the mixture is filtered. The organic phase is washed with water (30 ml) twice and evaporated. The residue is subjected to flash-chromatography on silica (75 g) during with heptane to afford 5.3 g (21.6 mmol. 58%) of N-(2′-chloro-6′-methylphenyl)-4-ethylaniline as an almost colourless liquid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationis filtered
  3. washThe organic phase is washed with water (30 ml) twice
  4. customevaporated

Sources & evidence

ORD record
ord-2b33856e70c240eb9300a12f92473264
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

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