Nitric Acid → 2-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

HRID 1781811

반응식

HRID 1781811 반응식
[N+:1]([O-:4])(O)=[O:2].[Br:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1)=[O:8]>C(O)(=O)C>[Br:5][CH2:6][C:7]([C:9]1[CH:14]=[C:13]([N+:1]([O-:4])=[O:2])[C:12]([OH:15])=[C:11]([O:16][CH3:17])[CH:10]=1)=[O:8]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 135422582-Bromo-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

생성물 1

HCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

A solution of 38 g of fuming nitric acid (96%) in 50 ml of glacial acetic acid is added dropwise while stirring and within 30 minutes at 20°-25° to a solution of 112.5 g of 2-bromo-4'-hydroxy-3'-methoxyacetophenone in 560 ml of glacial acetic acid. Yellow-brown crystals thereby separate. After 90 minutes the reaction mixture is poured on to 300 g of ice. The crystals are filtered under suction, washed with 1000 ml of water and dissolved in 1000 ml of methylene chloride. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the filtrate is evaporated at 50° in a water-jet vacuum until crystallization begins. The crystallizate, cooled to room temperature, is removed by filtration under suction and washed with a small amount of methylene chloride. There is obtained 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone of m.p. 147°-149°.

후처리

  1. customYellow-brown crystals thereby separate
  2. additionAfter 90 minutes the reaction mixture is poured on to 300 g of ice
  3. filtrationThe crystals are filtered under suction
  4. washwashed with 1000 ml of water
  5. dissolutiondissolved in 1000 ml of methylene chloride
  6. washThe organic phase is washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated at 50° in a water-jet vacuum until crystallization
  10. customis removed by filtration under suction
  11. washwashed with a small amount of methylene chloride

출처 및 근거

ORD 기록
ord-30f6d43a188b4882abf7f89bd21c9ed9
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05633371

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