Benzene, 1-(chloromethyl)-2-fluoro- → 4-(2-fluorophenyl)butan-2-one

HRID 971437Notes

Reaction equation

HRID 971437 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[C:10]([CH2:13]C(=O)C)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][CH2:11][C:10](=[O:12])[CH3:13]

Participants

5

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 128147004-(2-fluorophenyl)butan-2-oneYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2-fluorobenzyl chloride (22.47 g), acetylacetone (17.10 g), anhydrous potassium carbonate (21.5 g) and ethanol (155 ml) was heated at reflux for 18 hr. The solvent was evaporated and the residue was partitioned between water (200 ml) and ether (150 ml). The aqueous layer was washed with ether (3×150 ml). The extracts were combined, washed with brine (200 ml), dried (MgSO4) and evaporated. Distillation of the residue under reduced pressure gave the product (17 g) b.p. 58°-66°/0.5-0.6 mm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water (200 ml) and ether (150 ml)
  5. washThe aqueous layer was washed with ether (3×150 ml)
  6. washwashed with brine (200 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-8562daf21d714fed9030f5276501b741
Source dataset
uspto-grants-1979_07
Patent number
US04160036

Reaction notes

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