Réaction #595333

ord-5970614c3a9c4a1f96ec574ef8d59127

Équation de réaction

O=Cc1ccc(O)c(F)c1
3-fluoro-4-hydroxybenzaldehyde
OCCBr
2-bromoethanol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=Cc1ccc(OCCO)c(F)c1
3-Fluoro-4-(2-hydroxyethoxy)benzaldehyde

Solvants

Conditions de réaction

Température
150°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationThe mixture is then filtered
  2. 2
    Autrethe filtrate is freed from the solvent on a rotary evaporator
  3. 3
    workup.ADDITION20 ml of sat. aqueous sodium bicarbonate solution are added
  4. 4
    AutreThe phases are separated
  5. 5
    Séchagethe organic phase is dried over magnesium sulfate
  6. 6
    AutreThe solvent is removed on a rotary evaporator
  7. 7
    AutreThe product obtained
  8. 8
    Autreis used without further purification in the subsequent reaction

Mode opératoire

5.00 g (35.69 mmol) of 3-fluoro-4-hydroxybenzaldehyde are dissolved in 50 ml of dry DMF. 5.35 g (42.82 mmol) of 2-bromoethanol and 19.73 g (142.74 mmol) of potassium carbonate are added. The reaction mixture is stirred at 150° C. for 10 h. The mixture is then filtered, and the filtrate is freed from the solvent on a rotary evaporator. The residue is taken up in 30 ml of ethyl acetate, and 20 ml of sat. aqueous sodium bicarbonate solution are added. The phases are separated and the organic phase is dried over magnesium sulfate. The solvent is removed on a rotary evaporator. The product obtained is used without further purification in the subsequent reaction.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09095582B2uspto-grants-2015_08