Dimethylformamide → Methyl 5-chloro-2-cyanobenzoate

HRID 397482Notes

Reaction equation

HRID 397482 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N>[Cl:12][C:9]1[CH:10]=[CH:11][C:2]([C:13]#[N:14])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 280500Methyl 2-Bromo-5-chlorobenzoate

Product 1

HCID 12052442Methyl 5-chloro-2-cyanobenzoate

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-bromo-5-chlorobenzoate (1.15 g, 4.6 mmol) in degassed DMF was added zinc cyanide (282 mg, 2.40 mmol) and palladium tetrakis triphenylphosphine (100 mg, 0.086 mmol) and the reaction is stirred at 90° C. over night. The reaction was partitioned between ethyl acetate and water. The organic was concentrated in vacuo and purified by flash chromatography eluting a gradient to 10 to 25% ethyl acetate in hexane yielding a white solid (methyl 5-chloro-2-cyanobenzoate).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. concentrationThe organic was concentrated in vacuo
  3. custompurified by flash chromatography
  4. washeluting a gradient to 10 to 25% ethyl acetate in hexane yielding a white solid (methyl 5-chloro-2-cyanobenzoate)

Sources & evidence

ORD record
ord-1b14c8b5e33b451ea05e7d10fbf852cd
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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