Nitric Acid → 4-Chloro-5-ethoxymethyl-2-fluoronitrobenzene

HRID 231419Notes

Reaction equation

HRID 231419 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[Cl:16])[CH3:6]>>[Cl:16][C:10]1[C:9]([CH2:8][O:7][CH2:5][CH3:6])=[CH:14][C:13]([N+:1]([O-:4])=[O:2])=[C:12]([F:15])[CH:11]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 145018362-Chloro-4-fluorobenzyl ethyl ether

Product 1

HCID 145018374-Chloro-5-ethoxymethyl-2-fluoronitrobenzene

Conditions

Temperature
-40 °C

Procedure

To a cooled (-40° C.) solution of fuming nitric acid (90%, 25 ml) was added dropwise 2-chloro-4-fluorobenzyl ethyl ether (2.5 g, 0.013 mole) at a rate which maintained the temperature at or below -40° C. Upon completion of addition, the reaction mixture was stirred for 15 minutes at -40° C. The reaction mixture was poured into ice (200 ml) and extracted with methylene chloride (7×40 ml). The extracts were combined, washed with water (2×40 ml), dried (magnesium sulfate) and concentrated under reduced pressure. The residue was passed through a column of silica gel eluting with ethyl acetate:heptane (1:9). Appropriate fractions were combined and concentrated under reduced pressure, yielding 1.07 g of 4-chloro-5-ethoxymethyl-2fluoronitrobenzene. The ir spectrum was consistent with the proposed structure.

Workup

  1. temperaturemaintained the temperature at or below -40° C
  2. additionUpon completion of addition
  3. extractionextracted with methylene chloride (7×40 ml)
  4. washwashed with water (2×40 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e399e30a9c794813a9d6ff38c3411ca0
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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