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

HRID 1730108Notes

Reaction equation

HRID 1730108 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 6228Dimethylformamide2×HCID 200424-tert-Butyl-2,6-dinitrophenolHCID 24386Thionyl Chloride2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

180 grams (0.75 moles) of 2,6-dinitro-4-tert-butylphenol thus prepared was placed in a mixture of 113 grams (0.95 moles) thionyl chloride, 55 grams (0.76 moles) 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-tert-butylchlorobenzene in the form of light yellow needles melting at 114° - 116° C.

Workup

  1. temperatureheated
  2. customwere removed under reduced pressure until a slush
  3. additionHexane was then added to the reaction vessel
  4. temperaturethe mixture cooled
  5. filtrationfiltered
  6. customThe product was then recrystallized

Sources & evidence

ORD record
ord-6ad76aa3af2f4c848fc14ae57b02d1de
Source dataset
uspto-grants-1976_11
Patent number
US03991116

Reaction notes

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