3-Bromopropionic acid → tert-Butyl 3-bromopropionate

HRID 1264391Notes

Reaction equation

HRID 1264391 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Br:15][CH2:16][CH2:17]C(O)=O>C1(C)C=CC=CC=1>[C:11]([O:10][C:6](=[O:5])[CH2:17][CH2:16][Br:15])([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 115533-Bromopropionic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine

Product 1

HCID 256128tert-Butyl 3-bromopropionateYield 80.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

28 g (138 mmol) N,N-dimethylformamide di-tert-butyl acetal was slowly added during 50 min to a solution of 5.3 g (34.5 mmol) 3-bromo-propionic acid in 50 ml toluene. The reaction was heated for further 30 min, cooled and extracted with H2O/toluene (2×), aqueous saturated NaHCO3 and aqueous saturated NaCl. The organic phase was dried over Na2SO4 and carefully (low boiling point of the product) evaporated to give 5.8 g (80%) of 3-bromo-propionic acid tert butylester [U. Widmer, A convenient preparation of tert-butyl esters. Synthesis (1983), Issue 2, 135-6].

Workup

  1. temperatureThe reaction was heated for further 30 min
  2. temperaturecooled
  3. extractionextracted with H2O/toluene (2×), aqueous saturated NaHCO3 and aqueous saturated NaCl
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customcarefully (low boiling point of the product) evaporated

Sources & evidence

ORD record
ord-1a092d828a134b98b5333ca91118a0eb
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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