2-BROMO-6-CHLORO-BENZOTHIAZOLE

General procedure: To a stirred suspension of CuBr (1.57 g, 10.9 mmol) in MeCN (25 ml) was added (Step 1) General procedure: The appropriately substituted 2-aminobenzothiazole (1.0 equiv) was suspended in acetonitrile (0.2 M). To this mixture was added copper (II) bromide (1.0 equiv) followed by t-butyl nitrite (1.3 equiv). After being allowed to stir at room temperature for 30 mm, the reaction mixture was diluted with EtOAc and washed with 1.0 M HC1 followed by brine. The organic phase was dried over MgSO4, filtered and concentrated before being purified by silica gel chromatography to provide the desired material.The following may be mentioned as examples of compounds of the formula (II): 2-chlorobenzothiazole, 2-bromobenzothiazole, 2-chlorobenzoxazole, 2-bromobenzoxazole, and 6-chloro-2-bromobenzothiazole.General procedure: To a stirred suspension of CuBr (1.57 g, 10.9 mmol) in MeCN (25 ml) was added tBuONO (1.63 ml, 13.7 mmol) and the mixture was stirred at 60 C for 10 min. Then 2-amino-6-methylbenzothiazole (14b) (1.50 g, 9.13 mmol) was added to the mixture, and the reaction mixture was stirred at 60 C for 1 h. After cooled to room temperature, the mixture was poured into 1 N HCl. The resulting precipitate was dissolved into EtOAc, washed with 1 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (7:1, v/v) as eluent to give the title compound (703 mg, 34%) as a brown oil.General procedure: A mixture of 2-bromo-6-methylbenzothiazole (15b) (703 mg, 3.08 mmol), methyl 4-amino-3-chlorophenylacetate (16a) (615 mg, 3.08 mmol), and PPTS (232 mg, 0.92 mmol) in xylene (10 ml) was refluxed for 10 h. After cooled to room temperature, the solvent was evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (6:1, v/v) as eluent to give methyl [3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl]acetate (274 mg, 26%) as a pale yellow oil

Molecular Weight:248.53
XLogP3:4.2
Hydrogen Bond Acceptor Count:2
Exact Mass:246.88581
Monoisotopic Mass:246.88581
Topological Polar Surface Area:41.1
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes