Ethanol → 2-(2-Bromo-4-fluorophenyl)-2-methylpropanoic acid

HRID 558115Notes

Reaction equation

HRID 558115 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:13])([CH3:12])[C:10]#N.[OH-:14].[Na+].C([OH:18])C>O1CCOCCOCCOCCOCCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:13])([CH3:12])[C:10]([OH:18])=[O:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 574450632-(2-Bromo-4-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 574450642-(2-Bromo-4-fluorophenyl)-2-methylpropanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Procedure

Mix 2-(2-bromo-4-fluoro-phenyl)-2-methyl-propionitrile (1 g, 4.13 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) (100 mg, 1% wt) with sodium hydroxide (10 M, 20 mL, 200 mmol) in ethanol (5 mL). Heat the mixture to reflux for 3 h. Quench the reaction with 1 N HCl. Extract the product with chloroform. Dry the organic phase over sodium sulfate and concentrate to give an oily residue. Purify the residue by FCC (10% methanol in DCM as eluant) to give the title compound as a yellow solid (1 g, 93%). MS (ES) m/z 260/262 [M+1]+.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 3 h
  3. customQuench
  4. customthe reaction with 1 N HCl
  5. extractionExtract the product with chloroform
  6. dry with materialDry the organic phase over sodium sulfate
  7. concentrationconcentrate
  8. customto give an oily residue
  9. customPurify the residue by FCC (10% methanol in DCM as eluant)

Sources & evidence

ORD record
ord-98a2dea87a274831a3a1b8eabb2555a2
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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