Dimethylformamide → 4-tert-Butyl-2,6-dinitrochlorobenzene

HRID 1678832Notes

Reaction equation

HRID 1678832 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1O)([O-:3])=[O:2].S(Cl)([Cl:20])=O.CN(C)C=O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1[Cl:20])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 200424-tert-Butyl-2,6-dinitrophenolHCID 24386Thionyl Chloride

Product 1

HCID 751764-tert-Butyl-2,6-dinitrochlorobenzeneYield 86.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

180 grams (.75 mole) of 2,6-dinitro-4-t-butylphenol thus prepared was placed in a mixture of 113 grams (.95 mole) thionyl chloride, 55 grams (0.76 mole) dimethylformamide and 300 ml. of dry toluene. The mixture was stirred and heated to reflux temperature for 15 hours, after which time the thionyl chloride, DMF and toluene were removed under reduced pressure until a slush remained. Hexane was then added to the reaction vessel, the mixture cooled and filtered. The product was then recrystallized from boiling hexane to give 168 grams 2,6-dinitro-4-t-butylchlorobenzene in the form of light yellow needles melting at 114°-116° C.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 15 hours
  3. customafter which time the thionyl chloride, DMF and toluene were removed under reduced pressure until a slush
  4. additionHexane was then added to the reaction vessel
  5. temperaturethe mixture cooled
  6. filtrationfiltered
  7. customThe product was then recrystallized

Sources & evidence

ORD record
ord-3c920e45dbf14124bd153236e10c6c98
Source dataset
uspto-grants-1978_03
Patent number
US04077795

Reaction notes

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