N-Methylaniline → HCID 86681320, compound

HRID 1778899Notes

Reaction equation

HRID 1778899 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Br:8][C:4]1[C:3]([CH3:9])=[C:2]([N:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 346812,6-Dibromotoluene

Product 1

HCID 86681320HCID 86681320, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

1,3-Dibromo-2-methylbenzene (5.01 g) and N-methylaniline (1.00 g) were added to toluene (65 mL). The solution was degassed and flushed with nitrogen three times. Cesium carbonate (9.12 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.872 g), and palladium (II) acetate (0.314 g) were added. The solution was degassed and flushed with nitrogen and then heated to 85° C. for 72 hours. The solution was cooled, added to 1 M aqueous HCl, and extracted with diethyl ether. The extract was washed with brine, dried on anhydrous sodium sulfate, filtered, and concentrated under vacuum. The crude material was purified on silica gel using 2% ethyl acetate in hexanes.

Workup

  1. customThe solution was degassed
  2. customflushed with nitrogen three times
  3. additionCesium carbonate (9.12 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.872 g), and palladium (II) acetate (0.314 g) were added
  4. customThe solution was degassed
  5. customflushed with nitrogen
  6. temperatureThe solution was cooled
  7. additionadded to 1 M aqueous HCl
  8. extractionextracted with diethyl ether
  9. washThe extract was washed with brine
  10. dry with materialdried on anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customThe crude material was purified on silica gel using 2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-70107b21c6a649689f5ac1c783984a49
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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