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

HRID 1389384Notes

Reaction equation

HRID 1389384 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-2deabee48ddb4ef6b4793ef1b990dea4
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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