Sulfuric Acid → 2,3-Dibromobenzaldehyde

HRID 1288451Notes

Reaction equation

HRID 1288451 reaction equation
BrBr.[Br:3][C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:11].S(=O)(=O)(O)[OH:13]>>[Br:3][C:4]1[C:9]([Br:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:11]=[O:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 346801,2-Dibromo-3-methylbenzene

Product 1

HCID 133810282,3-Dibromobenzaldehyde

Conditions

Temperature
100 °C

Procedure

Bromine (168 g., 1.05 mole) is added over about 1 hour, with vigorous stirring, to 117.5 g. (0.47 mole) of 2,3-dibromotoluene at 190° C. After the addition is complete, the mixture is cooled to 100° C., then 120 cc. of concentrated sulfuric acid is added and the mixture is stirred for 1 hour at 100° C. Temperature is raised to 140° C. for five minutes, then the mixture is cooled and the reaction is quenched in ice water. The solid is extracted into ether, and the ether extract is washed with water, then dilute aqueous sodium bicarbonate until the acid is completely removed, and filtered. Removing the ether by evaporation gives 2,3-dibromobenzaldehyde as the residue.

Workup

  1. customat 190° C
  2. additionAfter the addition
  3. temperatureTemperature is raised to 140° C. for five minutes
  4. temperaturethe mixture is cooled
  5. customthe reaction is quenched in ice water
  6. extractionThe solid is extracted into ether
  7. extractionthe ether extract
  8. washis washed with water
  9. customdilute aqueous sodium bicarbonate until the acid is completely removed
  10. filtrationfiltered
  11. customRemoving the ether
  12. customby evaporation

Sources & evidence

ORD record
ord-caf223e157494671b01b8ece5f28b950
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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