6-Bromo-2-chlorobenzothiazole

White solid

Iso-Pentyl nitrite (0.9 mL, 6.8 mmol) and copper (II) chloride (0.938 g, 5.5 mmol) were suspended in CHDMF (0.807 mL, 10.4 mmol) was added to phosphorous oxychloride (8.10 mL, 86.9 mmol), and the reaction mixture was stirred for 15 min. 6- bromobenzo[dlthiazol-2(3H)-one (2.00 g, 8.69 mmol) was added and the reaction mixture was heated to 100 A solution of 6-bromobenzothiazolin-2-one (500 mg, 2.2 mmol) in POCI3 (5 mE) was refluxed during 18 h, then poured onto ice. The solution was neutralized to pH 9 by addition of NH4OH, and the resulting solid collected by filtration. Washing with water and drying in vacuo gave 6-bromo-2-chlorobenzothiazole (450 mg, 83percent).General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20–25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20–25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.in an ice water bath, Under nitrogen protection, Sulfonyl chloride 20ml was added to 2-mercapto-5-bromobenzothiazole (2.46g, 10mmol).Reaction at room temperature for 2h, After testing without raw materials, Pour the mixture into 40g of ice water, Continue stirring, After the precipitate has been generated, stir it for 2 hours.Filter the precipitate, Wash with ice water, Vacuum dryingThe white solid 2-chloro-5-bromobenzothiazole 2.3g, yield 92percent.

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