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

HRID 450757Notes

Reaction equation

HRID 450757 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

To a mixed liquid of 4.86 g of methyl 5-(hydroxymethyl)thiophene-3-carboxylate and 50 ml of dichloromethane was added 4.12 ml of thionyl chloride under ice-cooling, followed by stirring at room temperature for 15 hours. The reaction solution was concentrated, added with ethyl acetate, and then washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was then evaporated to obtain 4.90 g of methyl 5-(chloromethyl)thiophene-3-carboxylate as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. additionadded with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated

Sources & evidence

ORD record
ord-9b2b94b3458b42a4b8e1df8de17406ea
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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