Methyl chloroformate → Methyl 5-methylthiophene-3-carboxylate

HRID 964931Notes

Reaction equation

HRID 964931 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

3

Reactant 2

HCID 6586Methyl chloroformateHCID 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 followed by treatment with an alkali azide, subsequent reduction and hydrolysis provides 5-(aminomethyl)thiophene-3-carboxylic acid (VI). ##STR38##

Sources & evidence

ORD record
ord-3c5661c1ca514df4b87078e618ecbe2d
Source dataset
uspto-grants-1998_06
Patent number
US05773411

Reaction notes

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