Chlorosuccinimide → 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-3-fluorobenzoic acid
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
Product 1
Reagents, catalysts & solvents 1
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)+.