Methyl iodide → Methyl 4,5-dibromo-3-methoxythiophene-2-carboxylate

HRID 450497Notes

Reaction equation

HRID 450497 reaction equation
IC.[C:3]([O-])([O-])=O.[K+].[K+].[Br:9][C:10]1[C:11]([OH:20])=[C:12]([C:16]([O:18][CH3:19])=[O:17])[S:13][C:14]=1[Br:15]>CN(C=O)C.C(OCC)C>[Br:9][C:10]1[C:11]([O:20][CH3:3])=[C:12]([C:16]([O:18][CH3:19])=[O:17])[S:13][C:14]=1[Br:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2777613Methyl 4,5-dibromo-3-hydroxythiophene-2-carboxylate

Product 1

HCID 2808414Methyl 4,5-dibromo-3-methoxythiophene-2-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

9.97 ml of a solution of iodomethane and then 29.44 g of K2CO3 are added, dropwise, to a solution of 34.35 g of methyl 4,5-dibromo-3-hydroxythiophene-2-carboxylate in 150 ml of DMF and the mixture is left to stir for 18 hours at AT. After cooling, the reaction mixture is diluted in 100 ml of ethyl ether and filtered, and the filtrate is concentrated under vacuum. The reaction crude is purified by silica gel chromatography, elution being carried out with heptane and then with a heptane/EtOAc mixture (85/15; v/v). 28.70 g of the expected compound are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated under vacuum
  4. customThe reaction crude
  5. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-8316e5bcded34f37960b332a2089cbd8
Source dataset
uspto-grants-2013_07
Patent number
US08486971B2

Reaction notes

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