Hydrochloric Acid → 2-Chloro-6-fluorobenzothiazole

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added 2-amino-6-fluorobenzothiazole (1.0017 g, 5.96 mmol, Sigma-Aldrich Chemical Company, Inc.), copper (II) chloride (1.201 g, 8.93 mmol, Sigma-Aldrich Chemical Company, Inc.), and tert-butyl nitrite (1.063 ml, 8.93 mmol, Acros Organics) in ACN and was heated to 65° C. for 2 hours. The reaction mixture was diluted with 1N HCl and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.9249 g, 4.93 mmol, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm s 7.45 (td, J=9.10, 2.74 Hz, 1 H) 7.97-8.07 (m, 2 H)

Provenance & Evidence