Ethylene Glycol → 2-[1-(4-Bromophenyl)cyclopropyl]acetic acid

HRID 1528837Notes

Reaction equation

HRID 1528837 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(CC#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[K+].Cl.[CH2:17]([OH:20])[CH2:18]O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:18][C:17]([OH:20])=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 665793142-[1-(4-Bromophenyl)cyclopropyl]acetonitrile

Product 1

HCID 665776222-[1-(4-Bromophenyl)cyclopropyl]acetic acid

Conditions

Temperature
180 °C

Procedure

[1-(4-Bromo-phenyl)-cyclopropyl]-acetonitrile (3.95 g, 16.73 mmol) and potassium hydroxide (3.75 g, 66.92 mmol) were combined in ethylene glycol (24 mL) and stirred at 180° C. overnight. The mixture was acidified with 6 N aqueous HCl and extracted three times with EtOAc. The combined organic layers were dried and concentrated to yield the title compound.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-81148ddb96b94b83b122698b55ca8e24
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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