Methyl 3-bromo-5-methylthiophene-2-carboxylate → 3-Cyano-5-methyl-thiophene-2-carboxylic acid methyl ester

HRID 1952646Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1Br)=[O:4].[Cu](C#N)[C:13]#[N:14]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:11])=[CH:8][C:9]=1[C:13]#[N:14])=[O:4]

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 3-Bromo-5-methyl-thiophene-2-carboxylic acid methyl ester (0.54 g, 2.3 mmol), and Copper cyanide (0.27 g, 2.99 mmol) in NMP (3 ml) was heated in a microwave at 220° C. for 30 min. The reaction mixture was cooled and diluted with EtOAc. The organic layer was washed with aqueous NH4OH, and brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (0-20% EtOAc in hexane) to give 0.31 g (74%) white solid.

Workup

temperatureThe reaction mixture was cooled
washThe organic layer was washed with aqueous NH4OH, and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe solid residue was purified by column (0-20% EtOAc in hexane)

Sources & evidence

ORD record: ord-c054268125104dcfb6c828274b4a818f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404859B2

Reaction notes

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