4-Fluorobenzyl chloride → 1-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanone

HRID 2307536Notes

Reaction equation

HRID 2307536 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1>[Cl-].[Zn+2].[Cl-].O>[C:1]([C:4]1[O:5][C:6]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([F:9])=[CH:11][CH:12]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 96024-Fluorobenzyl chlorideHCID 145052-Acetylfuran

Product 1

HCID 101306401-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanoneYield 74%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To 258 g (0.94 mol) of a 50% aqueous solution of zinc chloride were added 69.3 g of water, 99.0 g (0.90 mol) of 2-acetylfuran and 260 g (1.80 mol) of 4-fluorobenzylchloride. The mixture was stirred at 85° C. for 6 hours. The reaction mixture was cooled and extracted with ethylacetate. The extract was washed with 1N hydrochloric acid, washed with an aqueous sodium hydrogencarbonate solution and removed under reduced pressure. The obtained residue was distilled under reduced pressure to give 145.4 g of crude 2-acetyl-5-(4-fluorobenzyl)furan (106-121° C./0.4 mmHg). The crude product was recrystallized from isopropylalcohol/n-hexane to give 84.4 g of 2-acetyl-5-(4-fluorobenzyl)furan. Yield: 43%.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. washwashed with an aqueous sodium hydrogencarbonate solution
  5. customremoved under reduced pressure
  6. distillationThe obtained residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-bf1d1dbb5ef84e9db47ec2295b75da8f
Source dataset
uspto-grants-2004_12
Patent number
US06831177B1

Reaction notes

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