Dimethylformamide → Methyl 4-cyano-2-ethylbenzoate

HRID 514505Notes

Reaction equation

HRID 514505 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][CH3:13])[CH:3]=1.[CH3:14][N:15](C=O)C>[C-]#N.[C-]#N.[Zn+2].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:14]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][CH3:13])[CH:3]=1)#[N:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 53797189Methyl 4-bromo-2-ethylbenzoate

Product 1

HCID 66643778Methyl 4-cyano-2-ethylbenzoateYield 40%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Charged methyl 4-bromo-2-ethylbenzoate (1.9 g, 7.85 mmol), Zn(CN)2 (1.48 g, 12.56 mmol), Pd(PPh3)4 (1.0 g, 0.94 mmol) and DMF (30 mL) to a flask, the system was then purged with nitrogen and heated at 100° C. for 6 h. The reaction mixture was then filtered. The filtrate was extracted with ethyl acetate and concentrated the organic phase for flash column chromatograph to give 0.6 g of the title compound (40%). 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=7.6 Hz), 2.99 (2H, q, J=7.6 Hz), 3.92 (3H, s), 7.52-7.54 (1H, m), 7.57 (1H, s), 7.90 (1H, d, J=8.0 Hz).

Workup

  1. customthe system was then purged with nitrogen
  2. filtrationThe reaction mixture was then filtered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. concentrationconcentrated the organic phase for flash column chromatograph

Sources & evidence

ORD record
ord-630f8402e7564715886823994e9f6342
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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