Dimethylformamide → 5-Bromopyridine-2-carbonitrile

HRID 853804Notes

Reaction equation

HRID 853804 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][N:10](C=O)C>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 693532,5-Dibromopyridine

Product 1

HCID 8171545-Bromopyridine-2-carbonitrileYield 74%

Conditions

Temperature
120 °C

Procedure

Referring now to Scheme 3, a mixture of 2,5-dibromopyridine (20 mmol) and Cu(1)CN (20 mmol) in DMF (120 mL) was refluxed for 12 hr at 120° C. The reaction mixture was poured onto water and the solid which formed was extracted by using ethylacetate (250 mL, 3 times). The solvent was evaporated and the precipitate purified (SiO2, hexanes/EtOAc 90:10). Yield 74%, mp 125–126° C. 1H nmr (DMSO-d6); δ 8.03 (d, J=8.1 Hz, 1H), 8.37 (dd, J=8.1, 2.1 Hz, 1H). 8.92 (d, J=2.1 Hz, 1H). 13C nmr; δ 152.2, 140.6, 131.1, 130.3, 125.1, 117.0.

Workup

  1. additionThe reaction mixture was poured onto water
  2. customthe solid which formed
  3. extractionwas extracted
  4. customThe solvent was evaporated
  5. customthe precipitate purified (SiO2, hexanes/EtOAc 90:10)

Sources & evidence

ORD record
ord-7818c9c750514c44bc5ffc8e59b8a17a
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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