Formic Acid → 5-bromo-4-fluoro-1H-1,3-benzodiazole

HRID 475227Notes

Reaction equation

HRID 475227 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[OH-].[Na+].[CH:13](O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][CH:13]=[N:9][C:4]=2[C:3]=1[F:10]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 27832034-Bromo-3-fluorobenzene-1,2-diamine

Product 1

HCID 594744775-bromo-4-fluoro-1H-1,3-benzodiazoleYield 92%

Procedure

A mixture of 142 (25 g, 0.121 mol) and formic acid (75 mL) was heated to reflux for 1.5 h. After the completion of the reaction the reaction was cooled and made basic with 10% NaOH. The resulting solid was filtered and washed with water. Drying overnight under suction afforded 24 g (92%) of 5-bromo-4-fluoro-1H-benzoimidazole (144) as pale yellow solid which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customAfter the completion of the reaction the reaction
  4. temperaturewas cooled
  5. filtrationThe resulting solid was filtered
  6. washwashed with water
  7. customDrying overnight under suction

Sources & evidence

ORD record
ord-f1583a4b3fe34a2290845f9da677cef6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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