Acetic Acid → Ethyl 2-(2-bromothiophen-3-yl)acetate

HRID 2252266Notes

Reaction equation

HRID 2252266 reaction equation
C(Cl)(Cl)Cl.C(O)(=O)C.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10]1.C1C(=O)N([Br:27])C(=O)C1>O>[Br:27][C:10]1[S:9][CH:13]=[CH:12][C:11]=1[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 67184N-bromobutanimideHCID 520865Ethyl 3-thiopheneacetate

Product 1

HCID 67496474Ethyl 2-(2-bromothiophen-3-yl)acetateYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml 3-neck flask containing 50 ml of CHCl3 and 50 ml of glacial acetic acid, 9.5 grams (0.0558 mol) of ethyl thiophene-3-acetate was added, followed by 9.93 grams (0.0558 mol) of NBS. The mixture was stirred at room temperature for 12 hours. The mixture became clear yellow solution after 1 hour and then was cooled down to room temperature, and poured into 200 ml deionized (DI) water. The organic portion was washed again with 100 ml of DI-water, and then finally washed with 100 ml of 5% aqueous sodium bicarbonate solution. After having been dried over magnesium sulfate, the solvent was filtered and the product was concentrated under vacuum. The resulting residue was vacuum distilled at 95° C. under 1 mm mercury (Hg) yielding 12.3 grams of ethyl 2-bromothiophene-3-acetate (88% yield). 1H NMR (CDCl3): 1.26 (t, 3H), 3.60 (s, 2H), 4.16 (q, 2H), 6.93 (d, 1H), 7.22 (d, 1H).

Workup

  1. additionwas added
  2. customafter 1 hour
  3. temperaturewas cooled down to room temperature
  4. additionpoured into 200 ml
  5. washThe organic portion was washed again with 100 ml of DI-water
  6. washfinally washed with 100 ml of 5% aqueous sodium bicarbonate solution
  7. dry with materialAfter having been dried over magnesium sulfate
  8. filtrationthe solvent was filtered
  9. concentrationthe product was concentrated under vacuum
  10. distillationdistilled at 95° C. under 1 mm mercury (Hg)

Sources & evidence

ORD record
ord-7a41de87bbe64aa5a5ca497ddcf578f3
Source dataset
uspto-grants-2008_01
Patent number
US07321012B2

Reaction notes

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