Chlorosuccinimide → Methyl 3-(4-chloro-1H-pyrazol-5-yl)-4-methylbenzoate

HRID 1487912Notes

Reaction equation

HRID 1487912 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][N:15]=[CH:14][CH:13]=1.[Cl:17]N1C(=O)CCC1=O>ClCCCl>[Cl:17][C:13]1[CH:14]=[N:15][NH:16][C:12]=1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90030661Methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate2×

Product 1

HCID 90030357Methyl 3-(4-chloro-1H-pyrazol-5-yl)-4-methylbenzoateYield 34.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate (compound 51.1, 385 mg, 1.78 mmol) was dissolved in 1,2-dichloroethane (60 mL), then N-chlorosuccinimide (250 mg, 1.87 mmol) was added. The mixture was stirred at room temperature for 16 hours then washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; 0-20% EtOAc in hexanes) to yield 152 mg (34%) of the title compound as an oil. m/z (ES+) 251 (M+H)+. 1H NMR (400 MHz, Chloroform-d) δ 8.07-7.94 (m, 2H), 7.63 (d, J=0.7 Hz, 1H), 7.47-7.34 (m, 1H), 3.93 (s, 3H), 2.36 (s, 3H).

Workup

  1. washthen washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2; 0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eb2b205f505a476f87410d91b0466704
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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