Calcium Fluoride → Methyl 4-(fluoromethyl)benzoate

HRID 890657

反応式

HRID 890657 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 21866613Methyl 4-(fluoromethyl)benzoate収率 78.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-da8c24c5b365428ca729435422979881
出典データセット
uspto-grants-2006_02
特許番号
US06998412B2

関連ノート

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