Hydrochloric Acid → HCID 11412880, compound

HRID 2061027Notes

Reaction equation

HRID 2061027 reaction equation
Br[C:2]([CH3:10])([CH2:8][Br:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[Br:9]/[CH:8]=[C:2](\[CH3:10])/[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 246986ethyl 2,3-dibromo-2-methylpropanoate

Product 1

HCID 11412880HCID 11412880, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 37.7 g (137 mmol) of ethyl 2,3-dibromo-2-methylpropanoate in 176 ml of THF was added 25 ml of 1,8-diazabicyclo[5.4.0]-7-undecene and refluxed for 2 hours. After cooling to room temperature, to the mixture was added 1N HCl and extracted with tert-butyl methyl ether. The organic layer was washed sequentially with a saturated NaHCO3 solution and a saturated NaCl solution, dried over anhydrous MgSO4, and then concentrated under vacuum to obtain 23.8 g of (E)-ethyl 3-bromo-2-methyl-2-propenoate.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with tert-butyl methyl ether
  3. washThe organic layer was washed sequentially with a saturated NaHCO3 solution
  4. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c71a2ce9fb804d5aa7e4eb3d63156736
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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