Hydrochloric Acid → Methyl 3-(5-bromothiophen-2-yl)-3-oxopropanoate

HRID 654250Notes

Reaction equation

HRID 654250 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[C:9]([C:12]1[S:13][C:14]([Br:17])=[CH:15][CH:16]=1)(=[O:11])[CH3:10].Cl>C1COCC1.O>[Br:17][C:14]1[S:13][C:12]([C:9](=[O:11])[CH2:10][C:3]([O:6][CH3:7])=[O:8])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 793352-Acetyl-5-bromothiophene

Product 1

HCID 14456695Methyl 3-(5-bromothiophen-2-yl)-3-oxopropanoateYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (1.95 g of 60% dispersion in oil, 0.045 mol), dimethyl carbonate (50 mL) and THF (40 mL) were added to a flame dried flask equipped with stirrer and dropping funnel. 2-Acetyl-5-bromothiophene (5.0 g, 0.024 mol) in 20 mL THF was added dropwise. The mixture was then heated at reflux for 2 hours, then poured into 250 mL of water, acidified to pH 2.0 with 1N HCl and extracted 3×200 mL ether. The organic layers were combined, dried (MgSO4) and stripped to yield 6.4 g (99%) of present title product as an oil; tlc Rf 0.42 (CHCl3).

Workup

  1. customdried flask
  2. customequipped with stirrer
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 2 hours
  5. extractionextracted 3×200 mL ether
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-ac266a476b4c41ddb6eb57865d3c332b
Source dataset
uspto-grants-1992_07
Patent number
US05130379

Reaction notes

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