4-Bromo-3-methylaniline → 2-Bromo-N-(4-bromo-3-methylphenyl)acetamide

HRID 490161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490161
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[Br:10][CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+].ClCCl>[Br:10][CH2:11][C:12]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([CH3:9])[CH:4]=1)=[O:13]

Komponenten

5

Edukt 2

HCID 233594-Bromo-3-methylanilineHCID 89602Bromoacetyl chloride

Produkt 1

HCID 34164002-Bromo-N-(4-bromo-3-methylphenyl)acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

4-Bromo-3-methylaniline (10.08 g, 54.18 mmol) in 2N sodium hydroxide (200 mL) was treated with bromoacetyl chloride (5.00 mL, 60.8 mmol) as a solution in dichloromethane (200 mL) dropwise. After 15 minutes, the layers were separated. The organic phase was washed with 1N hydrochloric acid, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide 11.75 g (71%) of the title compound as a tan solid. 1H NMR (300 MHz, CDCl3) δ 2.39 (s, 3H), 4.01 (s, 2H), 7.23 (m, 1H), 7.44 (d, 1H, J=2.4 Hz), 7.49 (d, 1H, J=8.8 Hz), 8.07 (br s, 1H); MS (DCI/NH3) m/e 306 (M+H)+.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed with 1N hydrochloric acid
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-45205dd5906f42708ae7ebedd1da114c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528134B2

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