2-Chloro-6-methylaniline → N-(2'-chloro-6'-methylphenyl)-4-methylaniline

HRID 603337

反応式

HRID 603337 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Br[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 68972-Chloro-6-methylanilineHCID 78054-BromotolueneHCID 23676156Sodium t-butoxide

生成物 1

HCID 57952145N-(2'-chloro-6'-methylphenyl)-4-methylaniline収率 89.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

1.02 g (7.2 mmol) of 2-chloro-6-methylaniline, 1.23 g (7.2 mmol) 4-bromotoluene, 1.15 g (12 mmol) sodium tert-butoxide, 160 mg (0.7 mmol) tri-tert-butyhphosphine and 130 mg (0.23 mmol) bis-dibenzylideneacetone-palladium(0) are reacted in 50 ml toluene under nitrogen at 90° C. for 20 minutes and at 60° C. over night. Aqueous workup (3N HCl, with hyflo, washing the organic phase with water) and flash-chromatography on silica using heptan/toluene (4:1) as the eluent affords 1.49 g of N-(2′-chloro-6′-methylphenyl)-4-methylaniline.

後処理

  1. washAqueous workup (3N HCl, with hyflo, washing the organic phase with water) and flash-chromatography on silica

出典と根拠

ORDレコード
ord-3ceb3f1fa4cf4f2f8c4e63ebb615eccd
出典データセット
uspto-grants-2011_03
特許番号
US07906677B2

関連ノート

読み込み中…