3,4-Dimethylaniline → 3,4-Dimethyl-N-phenylaniline

HRID 749637ノート

反応式

HRID 749637 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]1([NH:5][C:4]2[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([CH3:1])[CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 72483,4-DimethylanilineHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

生成物 1

HCID 149586053,4-Dimethyl-N-phenylaniline

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒3 回

反応条件

温度
105 °C

実験手順

Into a 250 mL round bottom flask was placed palladium acetate (120 mg) and Cytop-216 (120 mg) and was stirred in toluene (20 mL) for 1 hour at room temperature under agron. To this was added, in order, 3,4-dimethylaniline (3.27 g), bromobenzene (6 mL), sodium t-butoxide (7.9 g) and a further (20 mL) of toluene. The resulting mixture was heated at 100-110° C. for between 4 and 6 hours. The mixture was cooled to room temperature and diluted with 20 mL of toluene, filtered to remove insolubles, and 10-20 g of Al2O3 was added. The resulting slurry was heated to −80° C. and filtered while hot. The toluene was removed by rotary evaporation and the residue was recrystallized from 150 mL of isopropyl alcohol. The solid produced on cooling was filtered by suction, washed with a further 100 mL of isopropyl alcohol, and dried overnight. Yield was 5.1 g with a purity >99% which was determined by HPLC and NMR.

後処理

  1. customInto a 250 mL round bottom flask was placed
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto remove insolubles, and 10-20 g of Al2O3
  5. additionwas added
  6. temperatureThe resulting slurry was heated to −80° C.
  7. filtrationfiltered while hot
  8. customThe toluene was removed by rotary evaporation
  9. customthe residue was recrystallized from 150 mL of isopropyl alcohol
  10. customThe solid produced
  11. temperatureon cooling
  12. filtrationwas filtered by suction
  13. washwashed with a further 100 mL of isopropyl alcohol
  14. customdried overnight

出典と根拠

ORDレコード
ord-227e0ad1f9c1476f9f07a4247666353e
出典データセット
uspto-grants-2008_07
特許番号
US07402700B2

反応ノート

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