N-bromobutanimide → 4-bromo-5-chloro-1,3-dimethyl-1H-pyrazole

HRID 2095690노트

반응식

HRID 2095690 반응식
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1.C1C(=O)N([Br:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:16][C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 5215075-Chloro-1,3-dimethylpyrazole

생성물 1

HCID 197442234-bromo-5-chloro-1,3-dimethyl-1H-pyrazole수율 52.2%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of 5-chloro-1,3-dimethyl-1H-pyrazole (0.500 g, 3.83 mmol) in carbon tetrachloride (2.0 mL) was charged with NBS (0.750 g, 4.21 mmol) and stirred at rt for 16 h. The reaction mixture was charged with silica gel and purified by chromatography on silica gel [ISCO Combiflash, 12 g cartridge, eluting with 100% heptane 10% EtOAc in heptane]. This resulted in 419 mg, 52% yield of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ=2.23 (s, 3H), 3.81 (s, 3H). MS (ES+): m/z 208.96, 210.93 (76/24) [MH+]. HPLC: tR=2.62 min (polar—5 min, ZQ3).

후처리

  1. additionThe reaction mixture was charged with silica gel
  2. custompurified by chromatography on silica gel [ISCO Combiflash, 12 g cartridge, eluting with 100% heptane 10% EtOAc in heptane]

출처 및 근거

ORD 기록
ord-13e0708973f44c2b957784d2ae99f458
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

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