Calcium Fluoride → Methyl 4-(fluoromethyl)benzoate

HRID 1796383

Reaction equation

HRID 1796383 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[F-:13].[K+].[F-].[Ca+2].[F-]>C(#N)C>[F:13][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 84512Calcium FluorideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 522689Potassium Fluoride

Product 1

HCID 21866613Methyl 4-(fluoromethyl)benzoateYield 78.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dry acetonitrile (150 ml) was added to 25.00 g of methyl 4-(bromomethyl)benzoate, 19.02 g of potassium fluoride and 9.51 g of calcium fluoride, and the mixture was heated to reflux for 3 days. The reaction solution was concentrated. After addition of 200 ml of acetonitrile, insolubles were removed by filtration, and the filtrate was concentrated again. The residue was purified by silica gel column chromatography (YMC•GEL® SIL-60-230/70, n-hexane:ethyl acetate=10:1–4:1), followed by distillation under reduced pressure to provide 14.45 g of the objective compound as colorless oil. B.p. 118.5–119° C./18 mmHg.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationThe reaction solution was concentrated
  4. additionAfter addition of 200 ml of acetonitrile, insolubles
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated again
  7. customThe residue was purified by silica gel column chromatography (YMC•GEL® SIL-60-230/70, n-hexane:ethyl acetate=10:1–4:1)
  8. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-afea607424f44c4689ffe3ea1b7a13de
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Linked notes

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