N,N-Dimethylaniline → tert-Butyl 2-bromopropanoate

HRID 2351185Notes

Reaction equation

HRID 2351185 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].CN(C)C1C=CC=CC=1.S(=O)(=O)(O)O.[C:21]([OH:25])([CH3:24])([CH3:23])[CH3:22]>C(Cl)(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:4]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 545327tert-Butyl 2-bromopropanoateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-bromopropionyl bromide (25 g.) in dry chloroform (50 ml.) was dropwise added with stirring and ice-cooling to a solution of N,N-dimethylaniline (24 g.) in t-butanol (11 g.) and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was poured into 6N sulfuric acid (150 ml.) and extracted with ether. The extract was in turn washed with 6N sulfuric acid, water, a 10% potassium carbonate aqueous solution and water and dried over magnesium sulfate. The solvent was distilled off to give oil of t-butyl 2-bromopropionate (21 g.).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washwashed with 6N sulfuric acid, water
  5. dry with materiala 10% potassium carbonate aqueous solution and water and dried over magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-70b07dcd81c14c548bcb394f63050ee4
Source dataset
uspto-grants-1989_10
Patent number
US04871860

Reaction notes

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