Sodium Hydroxide → 3-Bromo-4-cyanobenzoic acid

HRID 906048Notes

Reaction equation

HRID 906048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>ClCCl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23379143Methyl 3-bromo-4-cyanobenzoate

Product 1

HCID 534255203-Bromo-4-cyanobenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-bromo-4-cyanobenzoate (200 mg, 0.83 mmol) in dichloromethane (1.5 mL) and methanol (1.5) was added 1.0 N aqueous sodium hydroxide (1.7 mL, 1.7 mmol). The mixture was stirred vigorously for 2 h at room temperature. The volatile solvents were then removed in vacuo. The aqueous residue was acidified with 1 N aqueous hydrochloric acid and was then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to provide 3-bromo-4-cyanobenzoic acid (190 mg, 0.83 mmol, quantitative yield). 1H NMR (400 MHz, CDCl3): 8.42 (d, 1H), 8.15 (dd, 1H), 7.80 (d, 1H).

Workup

  1. customThe volatile solvents were then removed in vacuo
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-524347d40619444da414d386c38e63b3
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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