p-Fluorotoluene → HCID 59875330, compound

HRID 1703408Notes

Reaction equation

HRID 1703408 reaction equation
[Br-:1].[Br-:2].[Br-].[Al+3].BrBr.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1>O>[Br:1][C:9]1[C:10]([Br:2])=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[F:7]

Participants

5

Reactant 3

HCID 9603p-FluorotolueneHCID 24408BromineHCID 166749Bromhydrol

Product 1

HCID 59875330HCID 59875330, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

2.67 g of aluminum tribromide and 16.0 g of bromine were added to 110 g of 4-fluorotoluene, which had been cooled to -15° C. After increasing the temperature to +10° C., hydrolysis was carried out with water, the mixture was extracted by shaking with methylene chloride and the methylene chloride phase was washed and dried. After distilling off the solvent and the excess 4-fluorotoluene, 5.5 g of a mixture consisting of 88% of 2-bromo-4-fluorotoluene, 8% of 3-bromo-4-fluorotoluene and 4% of dibromo-4-fluorotoluene were obtained at a boiling point of 172° to 184° C. (normal pressure). Relative to the 4-fluorotoluene reacted, the yield of 3-bromo-4-fluorotoluene was 2.3%.

Workup

  1. temperatureAfter increasing the temperature to +10° C.
  2. customhydrolysis
  3. extractionthe mixture was extracted
  4. washthe methylene chloride phase was washed
  5. customdried
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-72eba121a3434b1a9905205adee68ca3
Source dataset
uspto-grants-1982_09
Patent number
US04351974

Reaction notes

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