Dinitrofluorobenzene → HCID 86739331, compound

HRID 1380276Notes

Reaction equation

HRID 1380276 reaction equation
[CH2:1]([OH:8])[C:2]#[C:3][C:4]#[C:5][CH2:6][OH:7].C([O-])([O-])=O.[K+].[K+].[N+:15]([C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1F)([O-:17])=[O:16].[K+].[Br-]>CC(C)=O.O>[CH2:1]([OH:8])[C:2]#[C:3][C:4]#[C:5][CH2:6][OH:7].[N+:15]([C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:19]=1[O:8][C:1]1[CH:6]=[CH:5][C:4]([N+:15]([O-:17])=[O:16])=[CH:3][C:2]=1[N+:24]([O-:26])=[O:25])([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 94973Diacetylene glycolHCID 253877Potassium Bromide

Product 1

HCID 86739331HCID 86739331, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2,4-hexadiyn-1,6-diol (1.1 g) in acetone (15 ml), K2CO3 (0.5 g) was added. To the stirred solution at room temperature, 2,4-dinitrofluorobenzene (3.8 g) was added gradually and the dark red solution stirred overnight at room temperature. It was poured into excess water, the pale yellow solid filtered off, washed with water and dried. Recrystallization from dioxane ethanol gave short, light pink needles, m.p. 210° C. (4.2 g, 95%). I.R. (KBr): 1592, 1333, 834 (Ar-NO2)cm-1.

Workup

  1. filtrationthe pale yellow solid filtered off
  2. washwashed with water
  3. customdried
  4. customRecrystallization from dioxane ethanol
  5. customgave short

Sources & evidence

ORD record
ord-7d51686eb35d4edaa961cfd386fa67b3
Source dataset
uspto-grants-1986_04
Patent number
US04581315

Reaction notes

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