Bromine → 2-Bromo-6-nitro-1H-benzimidazole

HRID 2099898Notes

Reaction equation

HRID 2099898 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10](S)[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[Br:14]Br>CO.Br>[Br:14][C:10]1[NH:9][C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[N:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 178526473HCID 178526473, compound

Product 1

HCID 577966712-Bromo-6-nitro-1H-benzimidazoleYield 78%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 887MethanolSolvent

Conditions

Temperature
7.5 °C

Procedure

A suspension of 5.0 g (25.61 mmol) of 6-nitro-1H-benzimidazole-2-thiol in 30 ml of methanol and 10 ml of hydrogen bromide (48% in water) was cooled to 5-10° C. and admixed with 5.7 ml (111 mmol) of bromine. Subsequently, the mixture was stirred at 5-10° C. for 1.5 hours and poured onto ice-water. The red precipitate was filtered off with suction, washed with water and dried at 40° C. under reduced pressure. 4.82 g (78%) of the desired product were obtained.

Workup

  1. additionpoured onto ice-water
  2. filtrationThe red precipitate was filtered off with suction
  3. washwashed with water
  4. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-27d278947a774572a90fff758c4f3809
Source dataset
uspto-grants-2009_08
Patent number
US07569700B2

Reaction notes

Loading…