Fluoroacetic acid → HCID 86687829, compound

HRID 1622467Notes

Reaction equation

HRID 1622467 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH2:11])[C:3]=1[NH2:12].[F:13][CH2:14][C:15](O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[N:12]=[C:15]([CH2:14][F:13])[NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 5237Fluoroacetic acidHCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

Product 1

HCID 86687829HCID 86687829, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 250 mL round bottomed flask was added 3-bromo-5-nitrobenzene-1,2-diamine (6.75 g, 29.1 mmol) and 2-fluoroacetic acid (4.54 g, 58.2 mmol) in Toluene (100 mL). The solution was heated to reflux 48 h. The reaction was found to be incomplete so an additional equivalent of acid (2.25 g) was added and solution was heated 6 hours. The mixture was allowed to cool and was evaporated. The residue was dissolved in 20 ml of DCM and was filtered through a sintered glass funnel where a brown precipitate (5.5 g, 69%) was isolated to obtain 4-bromo-2-(fluoromethyl)-6-nitro-1H-benzo[d]imidazole (6.01 g, 21.93 mmol, 75% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.69 (s, 1H) 5.81 (s, 1H) 8.33 (d, J=2.02 Hz, 1H) 8.49 (br. s., 1H); LC/MS: MS (ES+) m/e 275 [M+H]+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux 48 h
  3. additionwas added
  4. temperaturesolution was heated 6 hours
  5. temperatureto cool
  6. customwas evaporated
  7. dissolutionThe residue was dissolved in 20 ml of DCM
  8. filtrationwas filtered through a sintered glass funnel where a brown precipitate (5.5 g, 69%)
  9. customwas isolated

Sources & evidence

ORD record
ord-6ec665b7eab64d88b6620c194fb0048c
Source dataset
uspto-grants-2014_07
Patent number
US08778937B2

Reaction notes

Loading…