Water → 3-Bromo-2-chloro-4,5-difluorobenzoic acid

HRID 414368Notes

Reaction equation

HRID 414368 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[C:5]#N.[OH2:13].S(=O)(=O)(O)[OH:15]>>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[C:5]([OH:15])=[O:13]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 140717963-Bromo-2-chloro-4,5-difluorobenzonitrile

Product 1

HCID 98383473-Bromo-2-chloro-4,5-difluorobenzoic acid

Conditions

Temperature
100 °C

Procedure

A solution of 3-bromo-2-chloro-4,5-difluorobenzonitrile (9.8 g) in concentrated sulfuric acid (10 ml) was stirred at 100° C. for 35 minutes. After cooling, 18N sulfuric acid (50 ml) and water (10 ml) were added to the reaction mixture. The reaction mixture was stirred at 100° C. for 4 hours and then poured into ice water (300 ml). The resulting precipitate was collected by filtration, washed with water sufficiently and recrystallized from dichloromethane-n-hexane to give the title compound (9.24 g) as colorless prisms, mp 137.5°-139.5 ° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water sufficiently
  4. customrecrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-de8ff113b7c54382ba5b6290bc363e9a
Source dataset
uspto-grants-1988_12
Patent number
US04791225

Reaction notes

Loading…