Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 2246785Notes

Reaction equation

HRID 2246785 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+].Cl.C([OH:18])C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:18])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Product 1

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

Conditions

Temperature
100 °C

Procedure

To a room temperature solution of 1-(4-bromophenyl)cyclopropanecarbonitrile from Step 1 (13 g) in ethyl alcohol (110 mL) was added a solution of 56 mL of sodium hydroxide (25% NaOH in water W/W). The mixture was heated at 100° C. overnight. It was cooled to room temperature and poured into ice and hydrogen chloride (1 N), and extracted with dichloromethane (2×100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo to yield the title compound.

Workup

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cc7c1380478b4617b477cdfc2786d6ff
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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