Dimethylformamide → Methyl 3-cyano-5-(trifluoromethyl)benzoate

HRID 1640146Notes

Reaction equation

HRID 1640146 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:17]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoate

Product 1

HCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoateYield 64%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of methyl 3-bromo-5-(trifluoromethyl)benzoate (5.10 g, 0.0180 mol), zinc cyanide (1.26 g, 0.0107 mol) and tetrakis(triphenylphosphine)palladium(0) (0.910 g, 0.000787 mol) in DMF (50 mL) was subjected to MWI for 20 min at 230° C. The solvent was evaporated and the residue was suspended in EtOAc. The organic solution was and washed with 1N HCl, water and brine, dried and concentrated. The residue was purified by column chromatography to give methyl 3-cyano-5-(trifluoromethyl)benzoate (2.67 g, 64%) as white solid. 1H NMR (400 MHz, CDCl3) δ: 8.50-8.52 (m, 2H), 8.09 (m, 1H), and 4.03 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. washwashed with 1N HCl, water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-63466416da5b4ec0a31c39667e5b3913
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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