Isobutylene → tert-Butyl 2-bromo-2-methylpropionate

HRID 1384053Notes

Reaction equation

HRID 1384053 reaction equation
[CH2:1]=[C:2]([CH3:4])[CH3:3].[Br:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8].FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[Br:5][C:6]([CH3:11])([CH3:10])[C:7]([O:9][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:8]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 62406Trifluoromethanesulfonic acidHCID 749242-Bromo-2-methylpropanoic acid

Product 1

HCID 90290tert-Butyl 2-bromo-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutene is condensed into a solution of 2-bromo-2-methylpropanoic acid (10 mmol) and trifluoromethane sulfonic acid (0.1 mmol) in 100 mL of CH2Cl2 until the starting material is consumed, as observed by TLC. The volatile components are evaporated in vacuo, and the residue is filtered through a pad of neutral alumina using 50% ether/hexane. The filtrate is concentrated in vacuo and used without further purification.

Workup

  1. customis consumed
  2. customThe volatile components are evaporated in vacuo
  3. filtrationthe residue is filtered through a pad of neutral alumina using 50% ether/hexane
  4. concentrationThe filtrate is concentrated in vacuo
  5. customused without further purification

Sources & evidence

ORD record
ord-a7c89d2ba91b429f9bfcdaeaca4f31aa
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Reaction notes

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