Réaction #41719

Équation de réaction

bromine

5-methoxy-2-mercaptobenzothiazole

water

→

title compound

2-bromo-5-methoxybenzothiazole

Solvants

chloroform

ether

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred for further 20 min
2. 2
   FiltrationThe mixture was filtered
3. 3
   Autreto remove a cream solid
4. 4
   AutreThe organic phase was dried
5. 5
   Autreevaporated
6. 6
   Autreto leave a brown solid
7. 7
   Filtrationfiltered
8. 8
   LavageThe residue was washed with ether
9. 9
   Autreevaporated
10. 10
    Autrechromatographed (4:1 hexanes and ethyl acetate)

Mode opératoire

A solution of bromine (3.6 eq) in chloroform (0.75M) was added dropwise over a of 1 hr to a stirred suspension of 5-methoxy-2-mercaptobenzothiazole (1 eq) in form at 0° C. The mixture was stirred for 30 min before it was added slowly to water and stirred for further 20 min. The mixture was filtered to remove a cream solid. The organic phase was dried and evaporated to leave a brown solid. The brown solid was dissolved in ether and filtered. The residue was washed with ether and the filtrate and washings were combined and evaporated, chromatographed (4:1 hexanes and ethyl acetate) to give the title compound as a pale yellow solid. MS: MH+=244

Source