Methyl chloroformate → Methyl 5-methylthiophene-3-carboxylate

Reaction equation

Br[C:2]1[CH:6]=[C:5]([CH3:7])[S:4][CH:3]=1.Cl[C:9]([O:11][CH3:12])=[O:10]>>[CH3:7][C:5]1[S:4][CH:3]=[C:2]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=1

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 6385844-Bromo-2-methylthiophene

Product 1

HCID 4644182Methyl 5-methylthiophene-3-carboxylate

Procedure

Alternatively, initial lithiation of 3-bromo-5-methylthiophene followed by capture with methyl chloroformate gives methyl 5-methylthiophene-3-carboxylate. Free-radical bromination of the methyl group provides 5-(bromomethyl)thiophene-3-carboxylic acid. ##STR46##

Sources & evidence

ORD record: ord-555c32ff7e104301aea6374995d0faf5
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563158

Reaction notes

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