Reacción #1687646

ord-298d9a9657ed43e4b2558022df81d04e

Ecuación de reacción

CC(=O)Oc1ccc(C(=O)O)c(F)c1
4-acetoxy-2-fluorobenzoic acid
O=S(Cl)Cl
thionyl chloride
CCC(CC)OC(=O)c1ccc(OC(C)=O)cc1F
4-acetoxy-2-fluoro-1-(1-ethylpropyloxycarbonyl)benzene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto react
  2. 2
    Temperaturaunder reflux for 5 hours
  3. 3
    workup.DISTILLATIONThereafter, excessive thionyl chloride was distilled off
  4. 4
    workup.ADDITIONa mixture comprising 1 ml of pyridine, 4 ml of dry ether and 0.6 g of 3-pentanol was added dropwise to the above mixture
  5. 5
    workup.ADDITIONAfter the addition
  6. 6
    workup.ADDITIONdiluted with 200 ml of ether
  7. 7
    Lavadoan organic layer was washed consecutively with diluted hydrochloric acid
  8. 8
    Secadoa 1N sodium hydroxide aqueous solution and water, and dried over magnesium sulfate

Procedimiento

1.0 Gram of 4-acetoxy-2-fluorobenzoic acid was added to 7 ml of thionyl chloride, and the mixture was allowed to react under reflux for 5 hours. Thereafter, excessive thionyl chloride was distilled off, and a mixture comprising 1 ml of pyridine, 4 ml of dry ether and 0.6 g of 3-pentanol was added dropwise to the above mixture. After the addition, the resulting mixture was stirred at room temperature for one day and diluted with 200 ml of ether, and an organic layer was washed consecutively with diluted hydrochloric acid, a 1N sodium hydroxide aqueous solution and water, and dried over magnesium sulfate.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05976409uspto-grants-1999_11