Formic Acid → 6-bromo-1-phenyl-1H-benzo[d]imidazole

To a stirred mixture of 4-bromo-N2-phenyl-benzene-1,2-diamine (step A) (420 mg, 1.6 mmol) and trimethyl orthoformiate (4.8 g, 5 ml, 45.2 mmol), formic acid (1.2 g, 1 ml, 26.1 mmol) was added at room temperature, and afterwards the reaction mixture was allowed to stir at for 2 h under reflux conditions. The reaction mixture was cooled to room temperature, evaporated and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml), dried (MgSO4) and evaporated. The crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2) to yield the title compound as an off-white solid (358 mg, 82%), MS (ISP) m/z=275.0 [(M+H)+].

1. additionwas added at room temperature
2. customevaporated
3. extractionextracted with ethyl acetate (2×40 ml)
4. washThe combined organic layers were washed with sat. sodium bicarbonate solution (20 ml) and brine (20 ml)
5. dry with materialdried (MgSO4)
6. customevaporated
7. customThe crude product (400 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 3:2)

ORD record

ord-2ec4f77597e749ca976ad1dac227bdae

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365550B2