Potassium Acetate → 2-Bromo-3-nitrobenzyl acetate

HRID 485563

반응식

HRID 485563 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

HCID 128530522-Bromo-3-nitrobenzyl acetate수율 51.1%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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°).

후처리

  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

출처 및 근거

ORD 기록
ord-97a9a6e7eac0461b80c6b1e62078f6e4
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536591

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