Potassium Acetate → 2-Bromo-3-nitrobenzyl acetate

HRID 1065582

反応式

HRID 1065582 の反応式
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11]Br.[C:13]([O-:16])(=[O:15])[CH3:14].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C.C(Cl)Cl>[C:13]([O:16][CH2:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Br:1])(=[O:15])[CH3:14]

参加物

6

反応物 2

HCID 517044Potassium AcetateHCID 110663422-Bromo-1-bromomethyl-3-nitrobenzene

生成物 1

HCID 128530522-Bromo-3-nitrobenzyl acetate収率 51.1%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of 2-bromo-1-bromomethyl-3-nitrobenzene (20.2 g, 0.0685 mole), potassium acetate (10.08 g, 0.103 mole), and tetrabutylammonium chloride (1.5 g) in 150 ml of acetonitrile was heated at reflux for six hours. The reaction mixture was cooled, filtered, and extracted with methylene chloride. The extract was evaporated to give a residue which was redissolved in methylene chloride and washed twice with 150 ml portions of saturated aqueous sodium chloride solution. The organic phase was passed through phase separation filter paper and evaporated to give a dark solid. The solid was purified by column chromatography on silica gel, elution with toluene, to give (2-bromo-3-nitrophenyl)methyl acetate as a yellow solid (9.6 g, mp 60°-63°).

後処理

  1. temperatureat reflux for six hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. extractionextracted with methylene chloride
  5. customThe extract was evaporated
  6. customto give a residue which
  7. washwashed twice with 150 ml portions of saturated aqueous sodium chloride solution
  8. customThe organic phase was passed through phase separation
  9. filtrationfilter paper
  10. customevaporated
  11. customto give a dark solid
  12. customThe solid was purified by column chromatography on silica gel, elution with toluene

出典と根拠

ORDレコード
ord-738849b5d755482fb6376107dfefb4c9
出典データセット
uspto-grants-1982_05
特許番号
US04329518

関連ノート

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