Allyl bromide → HCID 15549374, compound

HRID 1067750Notes

Reaction equation

HRID 1067750 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6])[CH:20]=[CH2:19]

Participants

5

Reactant 3

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

Product 1

HCID 15549374HCID 15549374, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-4-nitrobenzonitrile (5 g, 30.5 mmol) in DMF (20 ml), cesium carbonate (15 g, 45.7 mmol) and allyl bromide (3.15 mL, 35.6 mmol) were added. The reaction mixture was stirred at room temperature for 18 hours, then it was partitioned between ethyl acetate and water. The combined organic phase was dried and concentrated to give the desired product (5.85 g, 94%). EI-MS m/z 205 (M+).

Workup

  1. customit was partitioned between ethyl acetate and water
  2. customThe combined organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2e290a5dffc84322b30778fee0169c97
Source dataset
uspto-grants-2001_06
Patent number
US06248785B1

Reaction notes

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