Sulfuryl chloride → 3-Chloro-5-fluoro-4-hydroxybenzoic acid

HRID 1913088Notes

Reaction equation

HRID 1913088 reaction equation
S(Cl)([Cl:4])(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[OH:16])[C:10]([OH:12])=[O:11]>C(O)(=O)C.CN(C)C=O>[Cl:4][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([F:6])[C:15]=1[OH:16])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 674965383-Chloro-5-fluoro-4-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Sulfuryl chloride (4.7 mL) is added to a solution of 3-fluoro-4-hydroxy-benzoic acid (2.97 g) in acetic acid (20 mL) stirred at 50° C. in N,N-dimethylformamide (3 mL) at room temperature. The resulting solution is stirred for 2 h, prior to the addition of another portion of sulfuryl chloride (1.0 mL). The solution is stirred at 60° C. for another 1.5 h and then cooled to ambient temperature. The solution is poured into ice-cold water and the precipitate formed is separated by filtration, washed with ice-cold water, and dried at 50° C. to afford the title compound as a beige solid.

Workup

  1. stirringThe solution is stirred at 60° C. for another 1.5 h
  2. additionThe solution is poured into ice-cold water
  3. customthe precipitate formed
  4. customis separated by filtration
  5. washwashed with ice-cold water
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-b603f59bed9349749a2275dc90488290
Source dataset
uspto-grants-2013_12
Patent number
US08609690B2

Reaction notes

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