Chlorosuccinimide → 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-3-fluorobenzoic acid

HRID 2196417Notes

Reaction equation

HRID 2196417 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[Cl:17]N1C(=O)CCC1=O>C1COCC1>[Cl:17][C:12]1[CH:13]=[N:14][N:15]([CH3:16])[C:11]=1[C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59355006HCID 59355006, compound

Product 1

HCID 593549914-(4-chloro-1-methyl-1H-pyrazol-5-yl)-3-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzoic acid (196 mg, 0.89 mmol) and N-chlorosuccinimide (119 mg, 0.89 mmol) in THF (5 mL) was stirred in a sealed tube at 70° C. After 1 h, the solution was partitioned between H2O-DCM, the aqueous phase was adjusted to pH 3 and the aqueous phase was washed several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated under vacuum and used directly without further purification (192 mg, 85%): LC-MS (ES) m/z=255 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customused directly without further purification (192 mg, 85%)

Sources & evidence

ORD record
ord-4bb4946243c24169ad3cc488e38d88ff
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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