1,3-Dibromopropane → (3-Bromo-propyl)-(2-chloro4,6-dimethyl-phenyl)-amine

HRID 1246303

反応式

HRID 1246303 の反応式
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].C([Li])CCC.[Br:16][CH2:17][CH2:18][CH2:19]Br>O1CCOCC1>[Br:16][CH2:17][CH2:18][CH2:19][NH:4][C:3]1[C:5]([CH3:10])=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 1130332-Chloro-4,6-dimethylanilineHCID 178418339Butyllithium

生成物 1

HCID 21916144(3-Bromo-propyl)-(2-chloro4,6-dimethyl-phenyl)-amine収率 67.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of the 2-chloro-4,6-dimethyl aniline (16.9 g g, 108 mmol) in 1,4-dioxane (80 mL) was added n-butyl lithium solution (2.5 M in hexanes, 48 mL), dropwise, at 0° C. under argon. The reaction mixture was warmed up to rt and stirred for 20 min. 1,3-Dibromopropane (109 g, 543 mmol) was added and the reaction mixture was stirred overnight. The mixture was filtered through celite and concentrated. Purification was carried out by reverse phase chromatography using water, methanol and trifluoroacetic acid to obtain product (20.01 g, 72.5 mmol, 67%) as brown oil. LC/MS: tR=1.5 min. [M+H] 277. 1H NMR (CD3OD) δ: 7.12 (s, 1H), 6.99 (s, 1H), 3.52 (t, J=6.65 Hz, 2H), 3.36 (t, J=6.75 Hz, 2H), 2.36 (s, 3H), 2.29 (s, 3H), 2.14 (m, 2H).

後処理

  1. customat 0° C.
  2. stirringthe reaction mixture was stirred overnight
  3. filtrationThe mixture was filtered through celite and
  4. concentrationconcentrated
  5. customPurification

出典と根拠

ORDレコード
ord-ae5ebf9444f24fcbbdd77cd55a77b0e3
出典データセット
uspto-grants-2006_10
特許番号
US07125990B2

関連ノート

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