Ethanol → Ethyl 3-bromo-2,2-dimethylpropanoate

HRID 423301Notes

Reaction equation

HRID 423301 reaction equation
[Br:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:14][CH2:15]O>>[Br:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([O:6][CH2:14][CH3:15])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2719323-Bromo-2,2-dimethylpropanoic acid

Product 1

HCID 12373576Ethyl 3-bromo-2,2-dimethylpropanoate

Procedure

3-Bromo-2,2-dimethylpropanoic acid (200 mg) was dissolved in EtOH (5 ml) and treated with concentrated H2SO4 (0.4 ml). This mixture was heated at reflux overnight then evaporated. The residue was extracted from H2O with EtOAc (×2) and the combined organic solutions dried and evaporated to give the title compound (316 mg) as a clear oil. δH (CDCl3, 400 MHz) 1.20 (3H, t), 1.32 (6H, s), 3.51 (2H, s), 4.18 (2H, q).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux overnight
  3. customthen evaporated
  4. extractionThe residue was extracted from H2O with EtOAc (×2)
  5. customthe combined organic solutions dried
  6. customevaporated

Sources & evidence

ORD record
ord-a01ad34764be4e8ca509ba0e5feb857c
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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