Toluene → 3-Bromo-4-fluorobenzaldehyde

HRID 904793Notes

Reaction equation

HRID 904793 reaction equation
C1(C)C=CC=CC=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[C:12](Cl)=[O:13].[H][H]>[Pd].O>[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 1140TolueneHCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 1736043-Bromo-4-fluorobenzaldehydeYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

2 g of palladium/activated carbon (5% by weight of Pd) and 350 g of toluene are heated for 1 hour at 75° C. in a three-necked flask equipped with a gas inlet tube, a reflux condenser and a stirrer while water gas (CO:H2 =1) is being passed through. 70.0 g of 3-bromo-4-fluorobenzoyl chloride prepared as in Example 3 were then added and hydrogen was passed in instead of water gas. The temperature was increased to 85° C. After 4 hours 95% of the amount of hydrogen chloride expected had been split off. After cooling down, the reaction mixture was filtered and the filtrate was distilled off. 53 g of 3-bromo-4-fluorobenzaldehyde, boiling point 112° C./20 mbars, nD30 1.5685 and melting point: 30° C., were obtained.

Workup

  1. additionwere then added
  2. customAfter 4 hours 95% of the amount of hydrogen chloride expected had been split off
  3. temperatureAfter cooling down
  4. filtrationthe reaction mixture was filtered
  5. distillationthe filtrate was distilled off

Sources & evidence

ORD record
ord-8f5ccac8207f4fe1995a385fccc555b9
Source dataset
uspto-grants-1983_12
Patent number
US04420433

Reaction notes

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