Hydrochloric Acid → HCID 12993678, compound

HRID 1828020Notes

Reaction equation

HRID 1828020 reaction equation
[Br:1][C:2]1[C:3]([Cl:13])=[C:4]([C:8]([O:10]CC)=[O:9])[S:5][C:6]=1[Br:7].[OH-].[Li+].C1COCC1.Cl>O>[Br:1][C:2]1[C:3]([Cl:13])=[C:4]([C:8]([OH:10])=[O:9])[S:5][C:6]=1[Br:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 12993677HCID 12993677, compound

Product 1

HCID 12993678HCID 12993678, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Ethyl 4,5-dibromo-3-chlorothiophene-2-carboxylate (5.52 g, 15.8 mmol) and lithium hydroxide (0.716 g, 31.7 mmol) were taken up in mixture of THF (30 mL) and water (30 mL). The reaction mixture was stirred at 25° C. for 32 hours. The aqueous layer was made acidic by the dropwise addition of conc hydrochloric acid and extracted with ether (3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give the product as a white solid (4.38 g, 86%) that was used without purification: mp 209–223° C. (d); 1H NMR (CDCl3 and DMSO-d6) δ 4.15 (bs, 1H); EI/MS 320 m/e (M+).

Workup

  1. extractionextracted with ether (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdcb45e74d5a4b89bc9f568a1503e14e
Source dataset
uspto-grants-2006_06
Patent number
US07056940B2

Reaction notes

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