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

HRID 1392700Notes

Reaction equation

HRID 1392700 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-bd125fac3efa4568a1dc9fe09e4b8c1e
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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