Dinitrofluorobenzene → HCID 86739331, compound

HRID 1904050Notes

Reaction equation

HRID 1904050 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-b7b5fb3db19c450db7e530d585ac9b57
Source dataset
uspto-grants-1984_03
Patent number
US04439514

Reaction notes

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