1,2-Dibromoethane → 18721-65-8

HRID 2283427Notes

Reaction equation

HRID 2283427 reaction equation
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>CN(C=O)C>[C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])([C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 96345tert-Butyl ethyl malonateHCID 27341781-Butyl-3-methylimidazolium tetrafluoroborate

Product 1

HCID 8954485018721-65-8

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Step 1 A stirred suspension of tert-butyl ethyl malonate (2.01 mL, 10.6 mmol), 1,2-dibromoethane (1.01 mL, 11.7 mmol), potassium carbonate (3.67 g, 26.6 mmol) and 1-butyl-3-methylimidazolium tetrafluoroborate (0.198 mL, 1.06 mmol) in DMF (26.6 mL) was heated to 55° C. for 20 hours. Upon cooling the mixture was filtered and the solid residue was washed with Et2O. The mixture was diluted with Et2O and washed with water (×2). The organic phase was dried (Na2SO4), filtered and concentrated giving 1-tert-butyl 1-ethyl cyclopropane-1,1-dicarboxylate which was used without further purification, 2.24 g.

Workup

  1. temperatureUpon cooling the mixture
  2. filtrationwas filtered
  3. washthe solid residue was washed with Et2O
  4. additionThe mixture was diluted with Et2O
  5. washwashed with water (×2)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2fe9c339bf7741a6ba95a76a0914eea2
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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