Allyl bromide → HCID 15549374, compound

HRID 1532759Notes

Reaction equation

HRID 1532759 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([OH:9])[CH:8]=1)#[N:2].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:15]([O:9][C:7]1[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[N+:10]([O-:12])=[O:11])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 151119213-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 15549374HCID 15549374, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-cyano-2-nitro-phenol (3.0 g, 18.9 mmol), allyl bromide (1.82 ml, 21.0 mmol) and cesium carbonate (7.39 g, 22.7 mmol) in DMF (20 ml) was stirred at rt for 18 hrs under Ar. The reaction mixture was partitioned between t-butyl-methylether and water. The layers were separated and the aqueous portion was further extracted (×3). The combined organic extracts were washed twice with water, then brine and dried over MgSO4 and filtered. Removal of solvent at reduced pressure afforded the title compound (3.89 g, 100%). 1H NMR(400 MHz, CDCl3) δ 7.87 (d, J=8.5 Hz, 1H), 7.35 (dd, J=8.4 Hz J=1.2 Hz 1H), 7.35 (d, J=1.5 Hz, 1H), 6.02 (m, 1H), 5.52 (d, 1H), 5.43 (d, 1H), 4.73 (dd, J=3.6 Hz J=1.2 Hz 2H);

Workup

  1. customThe reaction mixture was partitioned between t-butyl-methylether and water
  2. customThe layers were separated
  3. extractionthe aqueous portion was further extracted (×3)
  4. washThe combined organic extracts were washed twice with water
  5. dry with materialbrine and dried over MgSO4
  6. filtrationfiltered
  7. customRemoval of solvent at reduced pressure

Sources & evidence

ORD record
ord-6ddeb23fa352459cb34e4d8d1440cd65
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

Loading…