Thionyl Chloride → Methyl 5-(chloromethyl)thiophene-3-carboxylate

HRID 1009477Notes

Reaction equation

HRID 1009477 reaction equation
O[CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1.S(Cl)([Cl:14])=O>ClCCl>[Cl:14][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12926498Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

Product 1

HCID 12926494Methyl 5-(chloromethyl)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.86 g of methyl 5-(hydroxymethyl)thiophene-3-carboxylate was dissolved in 50.0 mL of dichloromethane, and 4.12 mL of thionyl chloride was added thereto under ice-cooling, followed by stirring at room temperature for 15 hours. The reaction liquid was concentrated under reduced pressure, and to the obtained residue was added ethyl acetate, and then washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine. It was dried over anhydrous magnesium sulfate, and then the solvent was evaporated to obtain 4.90 g of methyl 5-(chloromethyl)thiophene-3-carboxylate.

Workup

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. additionto the obtained residue was added ethyl acetate
  5. washwashed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine
  6. dry with materialIt was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54a1ca223ad44f0b89855ad551186b9b
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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