Formic Acid → 5-Bromo-4-methyl-1H-benzo[d]imidazole

Participants

Role	Name	HCID	Charge
Reactant	Formic Acid	HCID 284	—
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Ammonium Hydroxide	HCID 14923	—
Reactant	4-Bromo-3-methylbenzene-1,2-diamine	HCID 59214273	—
Product	5-Bromo-4-methyl-1H-benzo[d]imidazole	HCID 59214444	98%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 156 (28 g, 140 mmol), formic acid (240 mL) and 37% concentrated HCl (400 mL) was heated to 60° C. for 12 h, cooled in an ice-water bath, and the pH slowly adjusted to 8-9 with 28% concentrated NH4OH. The solid was collected by filtration, washed with water and dried in air to afford 25 g (98%) of 5-bromo-4-methyl-1H-benzo[d]imidazole (158) as a yellow solid: MS (ESI) m/z=213 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637537B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-703b875ebec1469ab70aea33134791c1
Source note	uspto-grants-2014_01