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

HRID 1487912ノート

反応式

HRID 1487912 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eb2b205f505a476f87410d91b0466704
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

読み込み中…