Azobisisobutyronitrile → 4-Bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1294840ノート

反応式

HRID 1294840 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:7]=1)=[O:5])[CH3:2].[Br:26]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][Br:26])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:7]=1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58760952Ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-1h-pyrazole-3-carboxylate

生成物 1

HCID 587609464-Bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester収率 64%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester I-4a (2.8 g, 7.46 mmol), N-bromosuccinimide (1.6 g, 8.95 mmol), AIBN (245 mg, 1.49 mmol) in CCl4 (60 ml) was heated under reflux for 17 hours. The reaction was cooled to room temperature, filtered to remove any solids, and concentrated under vacuum. The crude residue was purified via silica gel chromatorgraphy (Flash 40) using a solvent gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to give the desired product (I-4b) as an amorphous solid (2.2 g, 64%): +APCI MS (M+1) 455.0.

後処理

  1. temperatureunder reflux for 17 hours
  2. filtrationfiltered
  3. customto remove any solids
  4. concentrationconcentrated under vacuum
  5. customThe crude residue was purified via silica gel chromatorgraphy (Flash 40)

出典と根拠

ORDレコード
ord-855fbb13045b45dd9952a942241ecefb
出典データセット
uspto-grants-2007_07
特許番号
US07241788B2

反応ノート

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