Water → HCID 22997669, compound

HRID 1166216Notes

Reaction equation

HRID 1166216 reaction equation
[Br:1]Br.[CH3:3][C:4]1[S:8][C:7]([C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Br:1][C:5]1[CH:6]=[C:7]([C:9](=[O:13])[C:10]([OH:12])=[O:11])[S:8][C:4]=1[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 14452584HCID 14452584, compound

Product 1

HCID 22997669HCID 22997669, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Br2 (0.665 mL, 12.9 mmol) was added dropwise to a solution of (5-methylthiophen-2-yl)-oxo-acetic acid (1.05 g, 6.15 mmol) and sodium acetate (757 mg, 9.23 mmol) in 10 ml of glacial acetic acid and stirred at room temperature for 6.5 hours. The reaction mixture was poured into 150 ml water and extracted with diethyl ether (2×75 ml). The combined diethyl ether layers were extracted with aqueous Na2S2O3, the organic layer was then dried over sodium sulfate, and concentrated under vacuum to provide crude (4-bromo-5-methylthiophen-2-yl)-oxo-acetic acid (1.40 g, 91%). 1H NMR (300 MHz, CDCl3) δ8.35 (1H, s), 2.54 (3H, s).

Workup

  1. extractionextracted with diethyl ether (2×75 ml)
  2. extractionThe combined diethyl ether layers were extracted with aqueous Na2S2O3
  3. dry with materialthe organic layer was then dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-68a392dfce6d420aa0b4b19850ac63c1
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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