Reaction #2460282

Reaction equation

sodium hydride

isatin

4-Bromoanisole

→

N-(4-methoxyphenyl)isatin

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   OtherA purple solution was formed which
2. 2
   Temperaturewarmed to room temperature
3. 3
   TemperatureThe reaction was heated in an oil-bath at 145° C. for 7 hours
4. 4
   TemperatureThe reaction was then cooled to room temperature
5. 5
   FiltrationThis suspension was filtered
6. 6
   Otherthe filtrate was evaporated to dryness
7. 7
   Othera very clean reaction
8. 8
   Othersuch for the next reaction

Procedure

A solution of isatin (2.5 g, 0.017 mol) in anhydrous DMF (50 ml) was cooled to 0° C. under a nitrogen atmosphere and treated with sodium hydride (0.5 g, 1.2 equivalents). A purple solution was formed which was stirred at 0° C. for 30 minutes and then warmed to room temperature. 4-Bromoanisole (2.13 ml, 1 equivalent) was added followed by copper iodide (6.46 g, 2 equivalents). The reaction was heated in an oil-bath at 145° C. for 7 hours. The reaction was then cooled to room temperature and diluted with an equal volume of ethyl acetate. This suspension was filtered and the filtrate was evaporated to dryness. TLC (1:4, ethyl acetate:hexanes) indicated a very clean reaction; Rf (product)=0.5. The crude material was used as such for the next reaction.

Source