Ethyl Acetate → HCID 51063911, compound

HRID 910773Notes

Reaction equation

HRID 910773 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(C)=O.[I-].[K+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromide

Product 1

HCID 51063911HCID 51063911, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-bromobenzylbromide (20.0 g, 80.0 mmol) in acetone (300 mL) was added 1,2,4-triazole (10.8 g, 120 mmol), potassium carbonate (11.0 g, 80.0 mmol) and potassium iodide (0.790 g, 4.72 mmol). The resulting white suspension was heated to 55° C. with vigorous stirring for 16 h. The yellow reaction mixture was cooled and ethyl acetate (100 mL) added. This was then washed with distilled water (100 mL×2), 1M NaOH(aq) (100 mL×2) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and solvent removed in vacuo to leave clear yellow oil. The crude product was purified by column chromatography (ethyl acetate) to give the title compound as a yellow crystalline solid (12.4 g, 65%),

Workup

  1. temperatureThe yellow reaction mixture was cooled
  2. washThis was then washed with distilled water (100 mL×2), 1M NaOH(aq) (100 mL×2) and brine (100 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customto leave clear yellow oil
  7. customThe crude product was purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-79142b02428542d7a2d0b8b0d6bb8b36
Source dataset
uspto-grants-2011_09
Patent number
US08022224B2

Reaction notes

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