Carbon tetrabromide → 4-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1862472ノート

反応式

HRID 1862472 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11]O)=[C:9]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[N:8]([CH:22]([CH3:24])[CH3:23])[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][Br:45])=[C:9]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[N:8]([CH:22]([CH3:24])[CH3:23])[N:7]=1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 693543045-(3,5-dichlorophenylthio)-4-hydroxymethyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

生成物 1

HCID 693555624-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester収率 62.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 504 mg 5-(3,5-dichlorophenylthio)-4-hydroxymethyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester in 5 ml of dichloromethane was added 375 mg of triphenylphosphine and 474 mg of carbon tetrabromide. The reaction mixture was stirred overnight. The solvent was removed and the residue was purified by flash chromatography on silica gel using diethyl ether/iso-hexane for the elution to give 367 mg of 4-bromomethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester as a colourless gum. Mass spectrum (ES) m/z 451 [M+H]+.

後処理

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography on silica gel
  3. washfor the elution

出典と根拠

ORDレコード
ord-b3b433b13407481f94a27ec444dd1119
出典データセット
uspto-grants-2003_03
特許番号
US06538015B1

反応ノート

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