Thionyl Chloride → 2-Thiophenecarboxylic acid, 5-(chloromethyl)-, methyl ester

To a solution of methyl 5-(hydroxymethyl)thiophene-2-carboxylate (1.440 g, 8.362 mmol) in anhydrous chloroform (7.5 ml) was added dropwise thionyl chloride (3.62 ml, 50.17 mmol) at 0° C. After stirring at room temperature for 1.5 hrs, the mixture was concentrated under reduced pressure. The residue was dissolved in anhydrous chloroform (10 ml), and the mixture was concentrated again under reduced pressure. This operation was repeated 3 times to remove thionyl chloride azeotropically. The residue was dried under reduced pressure to give crude methyl 5-(chloromethyl)thiophene-2-carboxylate (1.782 g) as a brown oil.

1. concentrationthe mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in anhydrous chloroform (10 ml)
3. concentrationthe mixture was concentrated again under reduced pressure
4. customto remove thionyl chloride azeotropically
5. customThe residue was dried under reduced pressure

ORD record

ord-f0cd830b6a464893a0c491d09d6d9129

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999989B2