Hydrochloric Acid → (3,5-Dibromothiophen-2-yl)-oxo-acetic acid

HRID 1166210Notes

Reaction equation

HRID 1166210 reaction equation
C([O:3][C:4](=[O:14])[C:5]([C:7]1[S:8][C:9]([Br:13])=[CH:10][C:11]=1[Br:12])=[O:6])C.Cl>CC(C)=O>[Br:12][C:11]1[CH:10]=[C:9]([Br:13])[S:8][C:7]=1[C:5](=[O:6])[C:4]([OH:14])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14113379Ethyl 3,5-dibromo-alpha-oxo-2-thiopheneacetate

Product 1

HCID 22997619(3,5-Dibromothiophen-2-yl)-oxo-acetic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3,5-Dibromothiophen-2-yl)-oxo-acetic acid ethyl ester (513 mg, 1.50 mmol) was dissolved in 25 ml acetone and treated with 15 ml 8 N HCl at reflux for a total of 4 hours. The reaction mixture was concentrated in vacuo, poured into 50 ml water, and extracted into 100 ml of dichloromethane. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield (3,5-dibromothiophen-2-yl)-oxo-acetic acid (467 mg, 99%). MS (M+H)+: 314.84; 1H NMR (300 MHz, DMSO-d6) δ7.64 (1H, s).

Workup

  1. temperatureat reflux for a total of 4 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionpoured into 50 ml water
  4. extractionextracted into 100 ml of dichloromethane
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bac93bc577a4939b2af6f105182e7bd
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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