Propyl mercaptan → Nitrobenzene

HRID 1085082Notes

Reaction equation

HRID 1085082 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1O.C(=O)([O-])[O-].[K+].[K+].C(S)CC.BrC(F)(F)C(F)(F)Br.[OH-].[Na+]>CN(C)C=O>[N+:8]([C:6]1[CH:7]=[CH:2][CH:3]=[CH:4][CH:5]=1)([O-:10])=[O:9]

Participants

7

Reactant 5

HCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 14798Sodium HydroxideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethane

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Into a pressure bottle was placed 2-chloro-4nitrophenol (15.0 g, 0.086 mole), potassium carbonate (11.9 g, 0.86 mole), propanethiol (1.5 g, 0.02 mole), 1,2-dibromotetrafluoroethane (33.7 g, 0.13 mole), and N,N-dimethylformamide (115 ml). The pressure bottle was sealed, and the mixture was stirred at 50° C. for 48 hours. The pressure bottle was cooled to room temperature, opened, and the contents poured into a separatory funnel. Approximately 200 ml of a 2N aqueous sodium hydroxide solution was added to the separatory funnel. The resultant mixture was extracted with four 300 ml portions of diethyl ether. The extracts were combined and washed with two 100 ml portions of a 2N aqueous sodium hydroxide solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, leaving an oil. The reaction described above was repeated three additional times. The residual oils form the four experiments were combined and purified by column chromatography on silica gel, eluting with n-heptane:toluene (95:5), yielding 57.6 g of 3-chloro-4-bromo-1,1,2,2-tetrafluoroethoxy)nitrobenzene as an oil.

Workup

  1. customThe pressure bottle was sealed
  2. temperatureThe pressure bottle was cooled to room temperature
  3. additionthe contents poured into a separatory funnel
  4. extractionThe resultant mixture was extracted with four 300 ml portions of diethyl ether
  5. washwashed with two 100 ml portions of a 2N aqueous sodium hydroxide solution
  6. extractionThe washed extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure
  10. customleaving an oil
  11. customThe residual oils form the four experiments
  12. custompurified by column chromatography on silica gel
  13. washeluting with n-heptane:toluene (95:5)

Sources & evidence

ORD record
ord-29df7cd7b46e4d3c9ad05fef7c0a2909
Source dataset
uspto-grants-1991_04
Patent number
US05008277

Reaction notes

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