Formic Acid → 5-Bromo-6-fluoro-1H-benzo(d)imidazole

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].[CH:11](O)=O>>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[NH:9][CH:11]=[N:10][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 284Formic Acid

HCID 199585604-Bromo-5-fluoro-1,2-benzenediamine

Product 1

HCID 532169315-Bromo-6-fluoro-1H-benzo(d)imidazole

Procedure

A mixture of 98 (600 mg, 2.93 mmol) in formic acid (5.0 mL) was heated to reflux overnight. The reaction mixture was concentrated in vacuo to afford a brown oil that was partitioned between EtOAc (300 mL) and a sat'd. aq. NaHCO3 (100 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo to afford 550 mg (87%) of 5-bromo-6-fluoro-1H-benzo[d]imidazole (100) as white solid (550 mg, 87%): MS (ESI) m/z=215 [M+1]+.

Workup

temperaturewas heated
temperatureto reflux overnight
concentrationThe reaction mixture was concentrated in vacuo
customto afford a brown oil that
customwas partitioned between EtOAc (300 mL)
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-82502aacda4948868c5516f8b4e84003
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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