Hydrochloric Acid → Methyl 5-cyano-2-hydroxybenzoate

HRID 1596440Notes

Reaction equation

HRID 1596440 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13]([Cu])#[N:14].Cl>CN(C=O)C>[C:13]([C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 77683Methyl 5-bromosalicylateHCID 178418546HCID 178418546, compound

Product 1

HCID 10583428Methyl 5-cyano-2-hydroxybenzoateYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 5-bromo-2-hydroxybenzoate (190.8 g; from step (a) above) and CuCN (73.9 g) were refluxed in DMF (500 mL) for 7 h. The temperature was allowed to decrease to 80° C. and HCl (500 mL) and FeCl3 (165.0 g) were added. The reaction mixture was stirred for 30 min., concentrated and partitioned between H2O and DCM. The organic layer was dried, concentrated the residue recrystallized from methylethyl ketone giving the sub-title compound in a 61% yield.

Workup

  1. customto decrease to 80° C.
  2. concentrationconcentrated
  3. custompartitioned between H2O and DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated the residue
  6. customrecrystallized from methylethyl ketone giving the sub-title compound in a 61% yield

Sources & evidence

ORD record
ord-fe35d0a2661347aa9c8dcfe65d75ff3b
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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