Sulfuric Acid → tert-Butyl 2-bromo-2-methylbutanoate

HRID 1632321Notes

Reaction equation

HRID 1632321 reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].[Br:5][C:6]([CH3:12])([CH2:10][CH3:11])[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.C(OCC)C>C(=O)([O-])O.[Na+]>[Br:5][C:6]([CH3:12])([CH2:10][CH3:11])[C:7]([O:9][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 8255IsobutyleneHCID 222500642-Bromo-2-methylbutyric acid

Product 1

HCID 20443643tert-Butyl 2-bromo-2-methylbutanoate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of about 40 ml of isobutene, 40 g of 2-bromo-2-methylbutyric acid, 1 ml of concentrated sulfuric acid, and 20 ml of dry ethyl ether was reacted in a closed tube overnight at room temperature. After the reaction was over, the reaction mixture was dispersed in a mixture of 150 ml of ice-water and 10 g of sodium hydrogencarbonate and extracted with 200 ml and then 100 ml of ether. The organic layers were collected, washed twice each time with 50 ml of water and then once with 50 ml of a saturated aqueous sodium chloride solution, and after drying with anhydrous magnesium sulfate, ether was distilled off to provide 36.3 g of tert-butyl 2-bromo-2-methylbutyrate.

Workup

  1. customwas reacted in a closed tube overnight at room temperature
  2. extractionextracted with 200 ml
  3. customThe organic layers were collected
  4. washwashed twice each time with 50 ml of water
  5. dry with materialonce with 50 ml of a saturated aqueous sodium chloride solution, and after drying with anhydrous magnesium sulfate, ether
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-4e8015c85df1449bb3c8a03524647595
Source dataset
uspto-grants-1984_10
Patent number
US04474779

Reaction notes

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