Réaction #992754

Équation de réaction

2-methoxy-6-methyl-phenylamine

N-bromosuccinimide

→

title compound

Rendement 26.0%

4-Bromo-2-methoxy-6-methyl-phenylamine

Rendement 26.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   FiltrationThe crude mixture was filtered through Celite
2. 2
   workup.ADDITIONdiluted with diethyl ether (200 mL)
3. 3
   Lavagewashed with sodium hydroxide (2 M, 2×100 mL) and brine (1×100 mL)
4. 4
   SéchageThe organic phase was dried over magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Autrepurified by flash chromatography

Mode opératoire

To 2-methoxy-6-methyl-phenylamine (10.0 g) dissolved in acetonitrile (200 mL) was added N-bromosuccinimide (14.3 g) and the reaction mixture was heated to 145° C. for 15 minutes in a sealed microwave process vessel. The crude mixture was filtered through Celite, diluted with diethyl ether (200 mL) and washed with sodium hydroxide (2 M, 2×100 mL) and brine (1×100 mL). The organic phase was dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 3.4 g (26%) of the title compound as a black solid. NMR (500 MHz, DMSO-d6): 2.06 (s, 3H), 3.77 (s, 3H), 4.55 (s, 2H), 6.78 (d, 1H), 6.82 (d, 1H).

Source