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

HRID 274455

Reaction equation

HRID 274455 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-745c37e8b9a244edb812e5d45f39b3bd
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Linked notes

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