2-Chloro-5-nitrobenzotrifluoride → 3-(Trifluoromethyl)-4-(benzyloxy)nitrobenzene

HRID 1862791Notes

Reaction equation

HRID 1862791 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1Cl.[CH2:15]([O:22]CC1C=CC=CC=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Na]>CS(C)=O.C(O)C1C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1[O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 612132-Chloro-5-nitrobenzotrifluorideHCID 66729449CID 66729449

Product 1

HCID 219520843-(Trifluoromethyl)-4-(benzyloxy)nitrobenzeneYield 866.3%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution containing 45.1 g (0.02 mole) of 3-(trifluoromethyl)-4-chloronitrobenzene in 100 ml of DMSO was added dropwise at ambient temperature a solution containing 26 g (0.2 mole) of sodium benzyloxide in 75 ml of benzyl alcohol causing the temperature to rise 40° C. After 48 hours at ambient temperature, the reaction mixture was poured into ice water and extracted with ether, and the extract was dried and concentrated to about 200 ml. To the concentrated solution was added 200 ml of hexane and the resulting solution was cooled. Filtration gave 51.5 g (87%) of colorless crystalline solid; m.p. 112°-114° C.

Workup

  1. additionwas added dropwise at ambient temperature a solution
  2. customto rise 40° C
  3. extractionextracted with ether
  4. customthe extract was dried
  5. concentrationconcentrated to about 200 ml
  6. additionTo the concentrated solution was added 200 ml of hexane
  7. temperaturethe resulting solution was cooled
  8. filtrationFiltration

Sources & evidence

ORD record
ord-a5e2389a08304d908583bbe7a85f047b
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

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