Sodium Hydroxide → 4-Bromo-2-methoxybenzoic acid

HRID 432255

Reaction equation

HRID 432255 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([O:10][CH3:11])[CH:3]=1.[OH-:12].[Na+].[O:14]1CCOCC1>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:14])=[O:12])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 223467024-Bromo-2-methoxybenzonitrile

Product 1

HCID 134507554-Bromo-2-methoxybenzoic acidYield 37%

Conditions

Temperature
100 °C

Procedure

4-Bromo-2-methoxybenzonitrile (7.35 g, 35 mmol) was dissolved in dioxane (400 mL). Sodium hydroxide (2.0 N, 200 mL) was added and the suspension was heated at 100° C. for 16 hours. Organic solvent was removed under reduced pressure and the aqueous mixture was filtered and washed with water. The filtrate was neutralized with hydrochloric acid (5.0N) to pH 1. The solid was collected by filtration to give 4-bromo-2-methoxybenzoic acid (3 g, 37%). 1H NMR (DMSO-d6) δ 3.84 (s, 3H), 7.21 (d, J=8.25 Hz, 1H), 7.33 (s, 1H), 7.58 (d, J=8.23 Hz, 1H).

Workup

  1. customOrganic solvent was removed under reduced pressure
  2. filtrationthe aqueous mixture was filtered
  3. washwashed with water
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-215c4d2fa9144088aa012f1c455182dd
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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