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

HRID 1295845

Reaktionsgleichung

Reaktionsgleichung von HRID 1295845
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 21916144(3-Bromo-propyl)-(2-chloro4,6-dimethyl-phenyl)-amineAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-714af1f63bde4ceeac146efc1d990d61
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244746B2

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