Methyl 4-bromo-2-methylbenzoate → Methyl 4-cyano-2-methylbenzoate

HRID 2277630Notes

Reaction equation

HRID 2277630 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[CH3:11].[C:13]([Cu])#[N:14]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([C:13]#[N:14])=[CH:6][C:5]=1[CH3:11]

Participants

3

Reactant 2

HCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 18766060Methyl 4-cyano-2-methylbenzoateYield 63%

Conditions

Temperature
180 °C

Procedure

A mixture of 4-bromo-2-methyl-benzoic acid methyl ester (26.0 g, 113.5 mmol) and CuCN (12.48 g, 140.7 mmol) was heated at 180° C. for 5 hours before it was poured into ice-water. The solid precipitate was collected by vacuum filtration to give a crude product which was then purified by column chromatography to afford the title compound (12.53 g, 63%) as a solid.

Workup

  1. filtrationThe solid precipitate was collected by vacuum filtration
  2. customto give a crude product which
  3. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-c16224f0099c4dc192b5dc129290a214
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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