Methyl 3-bromo-4-hydroxybenzoate → Methyl 3-cyano-4-hydroxybenzoate

HRID 1258328Notes

Reaction equation

HRID 1258328 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]([Cu])#[N:14]>CN1C(=O)CCC1.O>[C:13]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6])#[N:14]

Participants

5

Reactant 2

HCID 4778958Methyl 3-bromo-4-hydroxybenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoateYield 78.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of methyl 3-bromo-4-hydroxybenzoate (2.50 g, 10.775 mmol) in NMP (7.5 mL) was added CuCN (1.05 g, 11.853 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 200° C. for 4 h., cooled to RT, diluted with water (10 mL) and stirred for 10 min. The precipitated solid was filtered off and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford methyl 3-cyano-4-hydroxybenzoate (1.50 g, 78%) as a yellow solid.

Workup

  1. temperaturecooled to RT
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto obtain the crude product
  5. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-2ffdc15ff7b74f77b2f5a714d6e055f7
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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