Methyl iodide → 5-(2-bromo-4-chloro-6-fluoro-phenyl)-1-methyl-1H-tetrazole

Temperature

25 °C

A mixture of 5-(2-bromo-4-chloro-6-fluoro-phenyl)-2H-tetrazole (4.15 g, 14.95 mmol), K2CO3 (3.1 g, 22.43 mmol) and iodomethane (1.3 ml, 20.94 mmol) in DMF (30 ml) was stirred at 25° C. for 3 h. The mixture was partitioned between EtOAc (80 ml) and water (60 ml), the organic layer was separated, washed with water and brine, dried with Na2SO4 and concentrated. The remaining residue was purified by chromatography (silica gel; hexane/EtOAc 100:0-90:10) to obtain 5-(2-bromo-4-chloro-6-fluoro-phenyl)-1-methyl-1H-tetrazole as pale yellow solid (1.5 g, 35%) and the title compound (1.7 g, 39%) as reddish liquid. MS: 291.0 (MH+, 1Br).

1. customThe mixture was partitioned between EtOAc (80 ml) and water (60 ml)
2. customthe organic layer was separated
3. washwashed with water and brine
4. dry with materialdried with Na2SO4
5. concentrationconcentrated
6. customThe remaining residue was purified by chromatography (silica gel; hexane/EtOAc 100:0-90:10)

ORD record

ord-aa0513ef51d543ea9292dfee5c4a2f88

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592426B2