1-Bromo-2-Chloroethane → 1-(Pyridin-4-yl)cyclopropane-1-carboxylic acid

HRID 1698351Notes

Reaction equation

HRID 1698351 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.Br[CH2:12][CH2:13]Cl>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:8]([OH:10])=[O:9])[CH2:13][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 342284-Pyridineacetic acid

Product 1

HCID 552671091-(Pyridin-4-yl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of pyridin-4-yl-acetic acid (930 mg, 6.0 mmol) and 1-bromo-2-chloroethane (750 mg, 9.0 mmol) in 50% NaOH aq. solution (5 mL) is added benzyltriethylammonium chloride (680 mg, 3 mmol). The solution is heated to 60° C. and stirred at the temperature for 2 hours. After cooling down to rt, the aqueous layer is removed and the organic layer is neutralized with sat. NH4Cl aq. and extracted with Et2O. The combined organic phases are washed with H2O and dried over Na2SO4. Concentration under reduced pressure gives the title compound. The material is used in a next step without purification.

Workup

  1. temperatureAfter cooling down to rt
  2. customthe aqueous layer is removed
  3. extractionextracted with Et2O
  4. washThe combined organic phases are washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7b3c5e84698a4a1b92e141f58d7adfdd
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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