p-Fluoronitrobenzene → Methyl 3,5-bis(4-nitrophenoxy)benzoate

HRID 2396158Notes

Reaction equation

HRID 2396158 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>CN(C)C(=O)C>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([O:7][C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 22715471Methyl 3,5-bis(4-nitrophenoxy)benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of potassium carbonate (98.72 g, 0.714 mol) and 550 ml of N,N-dimethylacetamide (DMAC) is added to a 1L, three-necked round-bottom flask equipped with an overhead stirrer, condenser and a nitrogen inlet tube. Nitrogen is bubbled through the solution for 1 hour, following which methyl 3,5-dihydroxybenzoate (60.00 g, 0.357 mol) and 1-fluoro-4-nitrobenzene (100.79 g, 0.714 mol) are added. The slurry solution is stirred and heated to 80°-90° C. under nitrogen for 10 hours, and the mixture is then filtered while hot to remove inorganic salts. The filtrate is kept in a freezer overnight and the yellow crystals are collected by filtration, washed with water and dried. The product is recrystallized from ethyl acetate to yield 68 percent of yellow crystals: mp 180.5°-182.0° C.

Workup

  1. customequipped with an overhead stirrer, condenser and a nitrogen inlet tube
  2. customNitrogen is bubbled through the solution for 1 hour
  3. additionare added
  4. temperatureheated to 80°-90° C. under nitrogen for 10 hours
  5. filtrationthe mixture is then filtered while hot
  6. customto remove inorganic salts
  7. filtrationthe yellow crystals are collected by filtration
  8. washwashed with water
  9. customdried
  10. customThe product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-21d9dd07ed064c49984de04aebc76a2f
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

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