Hydrochloric Acid → 4-Chloro-2,6-difluorobenzoic acid

HRID 634686Notes

Reaction equation

HRID 634686 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:14]=[C:13]([F:15])[C:9]([C:10]([OH:12])=[O:11])=[C:8]([F:16])[CH:7]=1.[ClH:17]>S(=O)(=O)(O)O.C(O)(=O)C.O.[Cu]Cl>[Cl:17][C:6]1[CH:14]=[C:13]([F:15])[C:9]([C:10]([OH:12])=[O:11])=[C:8]([F:16])[CH:7]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 109759644-Amino-2,6-difluorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 177506844-Chloro-2,6-difluorobenzoic acidYield 98%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
15 °C

Procedure

A solution of sodium nitrite (220 mg, 3.18 mmol) in concentrated sulphuric acid (2 ml) was added over 15 minutes to a suspension of 4-amino-2,6-difluorobenzoic acid (550 mg, 3.18 mmol) in acetic acid (6 ml) at 15° C. The mixture was stirred at 15° C. for 1 hour then heated to 90° C. and poured into a solution of copper(I)chloride (800 mg) in concentrated hydrochloric acid (11 ml) at 95° C. The mixture was heated at 95° C. for 45 minutes and then allowed to cool. The mixture was diluted with water, extracted with ethyl acetate, the organic extracts dried (MgSO4) and the solvent removed by evaporation to give 4-chloro-2,6-difluorobenzoic acid (600 mg, 98%)

Workup

  1. temperaturethen heated to 90° C.
  2. temperatureThe mixture was heated at 95° C. for 45 minutes
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic extracts dried (MgSO4)
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-84cc276073634ca588a1e8caed7dcaad
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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