1,2-Dibromoethane → HCID 58198500, compound

HRID 545315Notes

Reaction equation

HRID 545315 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O.C1OCCOCCOCCOCCOCCOC1>[CH2:1]([O:3][C:4]([C:5]1([S:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=2)(=[O:7])=[O:8])[CH2:28][CH2:27]1)=[O:19])[CH3:2]

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 58198649HCID 58198649, compound

Product 1

HCID 58198500HCID 58198500, compoundYield 163%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 1.69 g (5.69 mmol) of (4-trifluoromethyl-benzenesulfonyl) -acetic acid ethyl ester (prepared according step 1 and 2 of Method A), 1.59 g (11.5 mmol) of potassium carbonate, 100 mg 18-crown-6 and 100 mg tetrabutylammonium bromide in acetone (40 mL) were added 0.49 mL (5.69 mmol) of 1,2-dibromoethane. The reaction was heated in a sealed tube to 65° C. for 18 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica, eluent heptanes, 0-20% ethyl acetate) to afford 2.99 g of 1-(4-trifluoromethyl -benzenesulfonyl)-cyclopropanecarboxylic acid ethyl ester.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica, eluent heptanes, 0-20% ethyl acetate)

Sources & evidence

ORD record
ord-0440cea5b09f43e0b618208f89fd8328
Source dataset
uspto-grants-2011_05
Patent number
US07935715B2

Reaction notes

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