Allyl bromide → 2-(3,4,5-Trifluorophenyl)-4-pentenoic acid

HRID 546688Notes

Reaction equation

HRID 546688 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[F:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[C:11]([F:14])[C:12]=1[F:13].C(Br)C=C.[OH-].[Na+]>C1COCC1.C(OCC)C>[F:6][C:7]1[CH:8]=[C:9]([CH:15]([CH2:3][CH:2]=[CH2:1])[C:16]([OH:18])=[O:17])[CH:10]=[C:11]([F:14])[C:12]=1[F:13]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 27779523,4,5-Trifluorophenylacetic acidHCID 178418339Butyllithium

Product 1

HCID 668391752-(3,4,5-Trifluorophenyl)-4-pentenoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (7.89 mL; 2.66 M solution in hexane) was added to a solution of 3,4,5-trifluorophenylacetic acid (2 g) in THF (50 mL) at −78° C. The reaction solution was stirred at −78° C. for 20 minutes. Then, the reaction solution was heated to 0° C. and further stirred for 30 minutes. Allyl bromide (0.999 mL) was added dropwise to the reaction solution, and the reaction solution was stirred at room temperature for three hours. A 1 N sodium hydroxide solution and diethyl ether were added to the reaction solution, and the aqueous layer was separated. 5 N hydrochloric acid and ethyl acetate were added to the resulting aqueous layer, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.45 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperatureThen, the reaction solution was heated to 0° C.
  2. stirringfurther stirred for 30 minutes
  3. stirringthe reaction solution was stirred at room temperature for three hours
  4. customthe aqueous layer was separated
  5. addition5 N hydrochloric acid and ethyl acetate were added to the resulting aqueous layer
  6. customthe organic layer was separated
  7. washThe resulting organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-6b4f518a6c8a427a8268ebc9cc57d732
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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