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

HRID 1293073

반응식

HRID 1293073 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-37c9ceb21e4d4abc8d8fe587992375b2
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238699B2

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