Hydrochloric Acid → 1-(4-Bromo-2-fluorophenyl)cyclopropane-1-carboxylic acid

HRID 1423997Notes

Reaction equation

HRID 1423997 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[C:4]([F:13])[CH:3]=1.[OH-:14].[K+].Cl.C([OH:19])C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:19])=[O:14])[CH2:10][CH2:9]2)=[C:4]([F:13])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 587623291-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

Product 1

HCID 666626821-(4-Bromo-2-fluorophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the compound (24.6 g, 102 mmol) obtained in Example 14-2) and potassium hydroxide (46 g, 820 mmol) in ethanol (200 ml) and water (40 ml) was heated to reflux for 7 h. The reaction mixture was cooled to room temperature, and then 5 N hydrochloric acid was added until the reaction mixture was rendered acidic. The deposited solid was collected by filtration, washed with water, and then dried to obtain the title compound (28.7 g, quant.) as a colorless solid.

Workup

  1. temperatureto reflux for 7 h
  2. filtrationThe deposited solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b9a9ff72194b4edead0db89d64755508
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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