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

HRID 655447Notes

Reaction equation

HRID 655447 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-656b7ed27d5847ea8e4019321fb7b8ba
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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