Nitric Acid → HCID 53879162, compound

HRID 1608556Notes

Reaction equation

HRID 1608556 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[N+:13]([C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1454243,5-Difluorophenylacetic acid

Product 1

HCID 53879162HCID 53879162, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 3,5-difluorophenylacetic acid (20 g, Fluorochem) in c.H2SO4 (150 ml) was stirred at -15° C. and c.HNO3 (75 ml) added dropwise over 1 hour at a temperature of from -5° to -10° C. The mixture was stirred for a further 1/2 hour at -10° C. and then poured into ice-water (1.0 1). The latter was extracted with ether (×3) and the combined extracts washed with water (×2), dried over MgSO4, and evaporated under reduced pressure to give a solid which was crystallised and then recrystallised from ether/hexane (1:4 v/v) to give 20.8 g of the desired product.

Workup

  1. extractionThe latter was extracted with ether (×3)
  2. washthe combined extracts washed with water (×2)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give a solid which
  6. customwas crystallised
  7. customrecrystallised from ether/hexane (1:4 v/v)

Sources & evidence

ORD record
ord-acb04a898b3344338e7e1e6dcbbf0b6c
Source dataset
uspto-grants-1995_03
Patent number
US05395853

Reaction notes

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