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

HRID 2095690ノート

反応式

HRID 2095690 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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]

出典と根拠

ORDレコード
ord-13e0708973f44c2b957784d2ae99f458
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

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