Pyrogallol → HCID 15044428, compound

HRID 1614720Notes

Reaction equation

HRID 1614720 reaction equation
[C:1]1([CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:3]=1[OH:4])[OH:2].[H-].[Na+].B(OCC)(OCC)OCC.[N+:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1F)([O-:24])=[O:23]>CN(C)C=O>[N+:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:2][C:1]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:3]=1[OH:4])([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 1057PyrogallolHCID 9009Triethyl borateHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 15044428HCID 15044428, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.9 g of pyrogallol, 380 ml of anhydrous dimethylformamide and 13.6 g of sodium hydride in suspension at 53% in oil were mixed together under an inert gas atmosphere and then stirred for 45 minutes at ambient temperature. 29 ml of triethyl borate were added, and the mixture was stirred for 30 minutes. Then, 17.6 ml of 2-nitro fluorobenzene were added over one hour at 0° C. followed by stirring for 20 hours at ambient temperature. The mixture was poured into a water-ice-N hydrochloric acid mixture and the precipitate was separated, washed with petroleum ether, taken up in ethyl ether and washed with N hydrochloric ac:id to obtain about 27 g of the expected product (Yield approx.: 76%) in the form of beige crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringby stirring for 20 hours at ambient temperature
  3. customthe precipitate was separated
  4. washwashed with petroleum ether
  5. washwashed with N hydrochloric ac

Sources & evidence

ORD record
ord-6ef85eb93f0e4d91bbb38f67ac25abc0
Source dataset
uspto-grants-1993_03
Patent number
US05198571

Reaction notes

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