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

HRID 1487912노트

반응식

HRID 1487912 반응식
[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]

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 90030661Methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate2회

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-eb2b205f505a476f87410d91b0466704
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428502B2

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