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

HRID 50012

반응식

HRID 50012 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6569Methyl Ethyl Ketone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-838b54af43ff4a799efbc77e83ff702c
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710077B1

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