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

HRID 1771470Notes

Reaction equation

HRID 1771470 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>[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

4

Reactant 2

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

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of methyl 3-bromo-4-hydroxybenzoate (2.50 g, 10.8 mmol) and CuCN (1.10 g, 12.3 mmol) in NMP (10 mL) was stirred at 200° C. under N2 atmosphere for 3 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was diluted in ethyl acetate (100 mL) and washed with water (50 mL×3) and brine (50 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=8/1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. additionThe filtrate was diluted in ethyl acetate (100 mL)
  4. washwashed with water (50 mL×3) and brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (PE/EtOAc=8/1)

Sources & evidence

ORD record
ord-7817f7879ba14cb2a5c4f52a99e3914a
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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