Methanol → 4-Bromo-2,6-dimethylbenzamide

HRID 2427496Notes

Reaction equation

HRID 2427496 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]#[N:7])=[C:4](Cl)[CH:3]=1.[OH-:12].[Na+].[CH3:14]O>>[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([C:6]([NH2:7])=[O:12])=[C:4]([CH3:14])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 566042454-Bromo-2-chloro-6-methylbenzonitrile

Product 1

HCID 544913594-Bromo-2,6-dimethylbenzamideYield 76%

Procedure

4-Bromo-2-chloro-6-methyl-benzonitrile (1.65 g, 7.16 mmol) was dissolved in methanol (20 mL) and 6M NaOH (20 mL) was added. The mixture was heated to reflux for seventeen hours. After cooling, the reaction was partitioned between diethyl ether and water. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Trituration with 10% EtOAc/Hexanes provided the title compound as a brick coloured solid (1.35 g, 76%). 1H NMR CDCl3: δ 7.41 (s, 1H), 7.29 (s, 1H), 6.33 (br s, 1H), 5.90 (br s, 1H), 2.37 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for seventeen hours
  3. temperatureAfter cooling
  4. customthe reaction was partitioned between diethyl ether and water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a4cd429cedf14183a37cb86bfbd4f936
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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