Reaktion #569520

Reaktionsgleichung

Isopropyl aniline

triethylamine

Bromoacetyl bromide

→

title compound

Ausbeute 99.8%

2-Bromo-N-isopropyl-N-phenyl-acetamide

Ausbeute 99.8%

Lösungsmittel

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 0°-5° C. with an ice-water bath
2. 2
   Sonstigetransferred to a separatory funnel
3. 3
   SonstigeThe organic layer is separated
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo

Vorschrift

Isopropyl aniline (8.00 g, 59.2 mmol) and triethylamine (8.26 mL, 59.2 mmol) are combined in anhydrousDCM (75 mL) under nitrogen and cooled to 0°-5° C. with an ice-water bath. Bromoacetyl bromide (5.16 mL, 59.2 mmol) is added dropwise over approximately 10 min. and the reaction is allowed to stir to ambient temperature overnight. The mixture is combined with aqueous HCl (50 mL 1N) and transferred to a separatory funnel. The organic layer is separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide the title compound as a brown solid (15.13 g, 59.1 mmol). 1H NMR (300 MHz, CDCl3) δ=1.08 (d, J=6.8 Hz, 6H); 3.53 (s, 2H); 4.92-5.01 (m, 1H); 7.18-7.54 (m, 5H). TLC Rf=0.22 (3:17 ethyl acetate: hexane).

Quelle