Phenol → 1-Chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene

HRID 50012

反応式

HRID 50012 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].C1(O)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22]

参加物

7

反応物 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenolHCID 700922-Butene, 1-bromo-3-methyl-2 回

生成物 1

HCID 129856901-Chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A reaction mixture of 2-chloro-5-nitrophenol (50.6 g), anhydrous potassium carbonate (44.5 g), tetrabutylammonium bromide (4.7 g) and 4-bromo-2-methyl-2-butene (53.3 g, 90%) in methyl ethyl ketone (263 mL) was stirred at ambient temperature overnight. TLC of the reaction mixture showed traces of phenol remaining. Additional prenyl bromide (1 mL) was then added to the reaction mixture and stirred for 2 hours. The solvent was then removed from the reaction mixture. The residue of the reaction mixture was then treated with water and extracted into diethyl ether. The extract was washed with 2N sodium hydroxide and water, dried (MgSO4), filtered, and evaporated, to leave a brown solid which was recrystallised from ethyl acetate/isopropyl alcohol to give 1-chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene, 49.5 g, a beige solid, a single spot on TLC (ethyl acetate:hexane, 20:80).

後処理

  1. stirringstirred for 2 hours
  2. customThe solvent was then removed from the reaction mixture
  3. additionThe residue of the reaction mixture was then treated with water
  4. extractionextracted into diethyl ether
  5. washThe extract was washed with 2N sodium hydroxide and water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a brown solid which
  10. customwas recrystallised from ethyl acetate/isopropyl alcohol

出典と根拠

ORDレコード
ord-838b54af43ff4a799efbc77e83ff702c
出典データセット
uspto-grants-2004_03
特許番号
US06710077B1

関連ノート

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