Hydrochloric Acid → (3,4,5-Tribromothiophen-2-yl)-oxo-acetic acid

HRID 1166212Notes

Reaction equation

HRID 1166212 reaction equation
C([O:3][C:4](=[O:15])[C:5]([C:7]1[S:8][C:9]([Br:14])=[C:10]([Br:13])[C:11]=1[Br:12])=[O:6])C.Cl>CC(C)=O.O>[Br:12][C:11]1[C:10]([Br:13])=[C:9]([Br:14])[S:8][C:7]=1[C:5](=[O:6])[C:4]([OH:15])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69968494(3,4,5-Tribromothiophen-2-yl)-oxo-acetic acid ethyl ester

Product 1

HCID 22997662(3,4,5-Tribromothiophen-2-yl)-oxo-acetic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of (3,4,5-tribromothiophen-2-yl)-oxo-acetic acid ethyl ester (0.4 g, 0.95 mmol) in acetone (10 ml), water (2 ml), and conc. HCl (8 ml) was stirred under reflux for 1.5 hours. The reaction mixture was allowed to cool to ambient temperature and concentrated in vacuo to remove acetone which gave rise to solids which were collected, washed with water and dried. (3,4,5-tribromothiophen-2-yl)-oxo-acetic acid was thus obtained as a light yellow solid (0.17 g, 49%). MS (M−H)−: 392.75; 13C NMR (75 MHz, CDCl3) δ124.19, 117.80, 113.26, 111.72. IR (KBr) cm−1 3477.9, 3107.1, 2922.5, 1715.9, 1681.5, 1666.0, 1484.5, 1306.5, 1268.9.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. customto remove acetone which
  4. customgave rise to solids which
  5. customwere collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bd26dfa5677b41c5bf4baec1fcf716b3
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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