Ethanol → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 1294370Notes

Reaction equation

HRID 1294370 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].CC[OH:17]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:17])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Product 1

HCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Conditions

Temperature
100 °C

Procedure

A mixture of nitrile (1 eq) from step 1, NaOH 25% (12 eq) in EtOH (0.5M) was heated to 100° C. for 5 h. The mixture was cooled to rt, quenched with AcOH and diluted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (hexane:EtOAc, 90:10 to 50:50) afforded the title compound.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customquenched with AcOH
  3. additiondiluted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-734a511db9fb4188b3c8b398efa69488
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

Loading…