Nitric Acid → HCID 18615641, compound

HRID 277410Notes

Reaction equation

HRID 277410 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[N+:27]([O-])([OH:29])=[O:28]>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:27]([O-:29])=[O:28])[C:5]([O:9][CH2:10][N:11]2[C:12](=[O:21])[C:13]3=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]3[C:15]2=[O:16])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18615657HCID 18615657, compound

Product 1

HCID 18615641HCID 18615641, compound

Procedure

2-Chloro-4-fluoro-5-(phthalimido)methoxybenzene (5.0 g, 16.4 mmol) was slowly added to a stirred mixture of con. sulfuric acid-con. nitric acid (10:1, 20 ml) at −20° C. Solution was then warmed to ambient temperature and allowed to stir for 1 hr. Addition to ice-water resulted in a light yellow precipitate which was separated by filtration. Column chromatography on silica gel in hexane-methylene chloride (3:7) furnished the title compound (3.2 g); 1H NMR (CDCl3, 300 MHz) 4.06 (3H, s), 7.54 (1H, d, J=8.5 Hz), 7.84 (2H, m), 7.97 (2H, m) ppm.

Workup

  1. customat −20° C
  2. customresulted in a light yellow precipitate which
  3. customwas separated by filtration

Sources & evidence

ORD record
ord-510120afe4bb409880b70e3b866e458c
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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