2-Bromoisovaleric acid → N-(4-bromo-2-fluorophenyl)valine

HRID 648289Notes

Reaction equation

HRID 648289 reaction equation
[K].Br[CH:3]([CH:7]([CH3:9])[CH3:8])[C:4]([OH:6])=[O:5].[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([F:18])[CH:12]=1.[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C@H:3]([C:4]([OH:6])=[O:5])[CH:7]([CH3:9])[CH3:8])=[C:13]([F:18])[CH:12]=1

Participants

6

Reactant 4

HCID 112682-Bromoisovaleric acidHCID 14798Sodium HydroxideHCID 1230504-Bromo-2-fluoroanilineHCID 5462222Potassium

Product 1

HCID 53711733N-(4-bromo-2-fluorophenyl)valine

Reagents, catalysts & solvents 1

HCID 21911965Chloroform etherSolvent

Procedure

To the potassium salt of α-bromoisovaleric acid (1.42 g) is added 4-bromo-2-fluoroaniline (1.9 g). The mixture is heated at 125° under nitrogen for 3.5 hr and then cooled to RT. The reaction product is poured into 2 M NaOH and ether/chloroform. The basic phase is separated and acidified with conc. HCl and then extracted into ether, washed with saturated NaCl solution, dried over calcium sulfate and evaporated to yield N-(4-bromo-2-fluorophenyl)valine.

Workup

  1. temperatureThe mixture is heated at 125° under nitrogen for 3.5 hr
  2. customThe basic phase is separated
  3. extractionextracted into ether
  4. washwashed with saturated NaCl solution
  5. dry with materialdried over calcium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-55668b77257f457abf0bd48c492ee5a8
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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