3-Fluorobenzoyl chloride → 3-Fluorobenzaldehyde

HRID 1358792Notes

Reaction equation

HRID 1358792 reaction equation
FC(F)(F)C1C=CC=C(C(F)(F)F)C=1.[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20].[H][H]>O>[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 743763-Fluorobenzoyl chlorideHCID 223106Benzene, 1,3-bis(trifluoromethyl)-HCID 178418361HCID 178418361, compound2×

Product 1

HCID 680093-FluorobenzaldehydeYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

0.5 g of 5% palladium on barium sulfate (recovered from Example 1) and 50 g of 3-fluorobenzoyl chloride were placed in a reaction vessel at room temperature with exclusion of water. A gentle stream of hydrogen gas was then introduced at atmospheric pressure. The mixture was subsequently heated to 80-90° C. and hydrogen gas was introduced continuously at atmospheric pressure. After liberation of acidic offgases had ceased (9.5 hours), the mixture was cooled to room temperature, the catalyst was removed by filtration and the filtrate was distilled at 28 mbar. At a boiling point of 73° C., 3-fluorobenzaldehyde was obtained in a yield of 23.0 g. This corresponds to a yield of 57% of theory.

Workup

  1. custom(9.5 hours)
  2. temperaturethe mixture was cooled to room temperature
  3. customthe catalyst was removed by filtration
  4. distillationthe filtrate was distilled at 28 mbar

Sources & evidence

ORD record
ord-a4732fe123cb489eab83d8017dac36a4
Source dataset
uspto-grants-2003_07
Patent number
US06596906B2

Reaction notes

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