Ethanol → 5-Bromo-2-chloro-4-methoxybenzoic acid

HRID 46229Notes

Reaction equation

HRID 46229 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([Cl:10])=C([CH:9]=1)C#N.[OH-:13].[Na+].[CH3:15][CH2:16][OH:17]>O>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][C:5]([Cl:10])=[C:15]([CH:9]=1)[C:16]([OH:13])=[O:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 672873335-Bromo-2-chloro-4-methoxybenzonitrile

Product 1

HCID 533294035-Bromo-2-chloro-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromo-2-chloro-4-methoxybenzonitrile (30.7 g, 124 mmol) and NaOH (127 g, 3.11 mol) in EtOH (500 mL) and water (250 mL) was refluxed overnight. After cooling to room temperature, EtOH was removed under reduced pressure. The mixture was diluted with water and neutralized with hydrochloric acid (3.0 N). The resulting solid was filtered and dried in vacuo to give title compound (32.9 g, quantitative) as a white solid.

Workup

  1. temperaturewas refluxed overnight
  2. customEtOH was removed under reduced pressure
  3. additionThe mixture was diluted with water and neutralized with hydrochloric acid (3.0 N)
  4. filtrationThe resulting solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-67e1beafb53e4152ada8f285e033e399
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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