Boron tribromide → 2-Bromo-1,3-benzothiazol-6-ol

Participants

Reaction Steps

2-Bromo-6-methoxy-1,3-benzothiazole (0.832 g, 3.41 mmol) was subjected to the procedure used for the preparation of 2-[2-(dimethylamino)pyrimidin-5-yl]-1,3-benzothiazol-6-ol, with the following exceptions: 4.4 equiv BBr3-solution was used, and after being stirred on, the mixture was poured into MeOH and then concentrated under reduced pressure. A slurry of this residue in EtOAc was filtered through silica and eluted with EtOAc/DCM/MeOH 10:10:1 and DCM/MeOH 9:1. The crude product was recrystallized from EtOAc to give 2-bromo-1,3-benzothiazol-6-ol (0.602 g). 1H NMR δ 10.00 (br s, 1H) 7.77 (d, 1H) 7.39 (d, 1H) 6.97 (dd, 1H).

Provenance & Evidence