Nitrobenzene → Benzene, 1-bromo-3-nitro-

HRID 1031778Notes

Reaction equation

HRID 1031778 reaction equation
Br(F)(F)F.[Br:5]Br.[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:9])=[O:8].S([O-])([O-])=O.[Na+].[Na+]>>[Br:5][C:12]1[CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 11457Benzene, 1-bromo-3-nitro-

Procedure

A vigorously stirred mixture consisting of 0.1 moles (5 ml) bromine-trifluoride and 0.12 moles (6.5 ml) of bromine was added into a brine cooled three-necked flask equipped with a magnetic stirrer and a condenser containing ca. 0.6-0.7 moles of nitrobenzene. The addition was carried out dropwise with vigorous stirring while the temperature was kept between zero and ten degrees centigrate. After the addition was completed the crude reaction mixture was poured into a stirred icy 5% sodium sulfite solution. The organic layer was separated, and the aqueous solution was extracted twice with two portions of 100 ml dichloromethane. The combined organic layer was washed with 5% sodium bicarbonate solution and successively with water. The organic phase was dried over anhydrous magnesium sulfate and the solvent evaporated. The crude reaction mixture was quantitatively analyzed by gas-chromatography internal standard program. The meta-bromonitrobenzene obtained was separated from the starting material by reduced pressure distillation. The yield of meta-bromonitrobenzene obtained, expressed in percentage of pure meta-bromonitrobenzene obtained based on reacted nitrobenzene, is 81%.

Workup

  1. additionwas added into a brine cooled three-necked flask
  2. customequipped with a magnetic stirrer and a condenser
  3. additionThe addition
  4. customwas kept between zero and ten degrees
  5. additionAfter the addition
  6. customreaction mixture
  7. customThe organic layer was separated
  8. extractionthe aqueous solution was extracted twice with two portions of 100 ml dichloromethane
  9. washThe combined organic layer was washed with 5% sodium bicarbonate solution and successively with water
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  11. customthe solvent evaporated
  12. customThe crude reaction mixture

Sources & evidence

ORD record
ord-6d90614b85cb4673bdb757bdf8d0d088
Source dataset
uspto-grants-1990_09
Patent number
US04954648

Reaction notes

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