Water → 6-(5-Bromo-furan-2-yl)-nicotinonitrile

HRID 853802Notes

Reaction equation

HRID 853802 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.[Br:14]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:14][C:5]1[O:1][C:2]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 111164736-(2-Furyl)nicotinonitrile

Product 1

HCID 109119016-(5-Bromo-furan-2-yl)-nicotinonitrileYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Continuing with Scheme 1, to a solution of 1 (5.1 g, 30 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (5.87 g, 33 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold-water. The precipitate that formed was collected, washed with water and dried to give the analytically pure product 2 in 90.4% yield, mp 196° C. 1H nmr (DMSO-d6); δ 6.86 (d, J=3.6 Hz, 1H), 7.38 (d, J=3.6 Hz, 1H), 7.86 (d, J=8.1 Hz, 1H), 8.33 (dd, J=8.1, 2.1 Hz, 1H). 8.98 (d, J=2.1 Hz, 1H). 13C nmr; δ 153.4, 152.7, 149.6, 140.9, 125.4, 117.9, 117.0, 115.0, 114.9, 106.9. MS (m/z, rel.int.); 248 (M+, 100), 220 (10), 169 (25), 141 (80), 114 (30). Calcd for C10H5BrN2O: C, 48.22; H, 2.02; N, 11.25. Found. C, 48.47; H, 2.01; N, 11.34.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customThe precipitate that formed
  3. customwas collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-91c6ee41b2ec43b68b31cd42421ce252
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

Loading…