Allyl bromide → 4-(Allyloxy)-5-bromo-2-chlorobenzonitrile

HRID 576320Notes

Reaction equation

HRID 576320 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:12](Br)[CH:13]=[CH2:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:11][C:3]1[C:2]([Br:1])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([Cl:10])[CH:4]=1)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile

Product 1

HCID 867140364-(Allyloxy)-5-bromo-2-chlorobenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 37 (20.5 g, 88.1 mmol), allyl bromide (11.2 mL, 132 mmol) and K2CO3 (24.4 g, 176 mmol) in acetone (440 mL) was stirred for 3 hours under reflux. The mixture was filtrated and concentrated in vacuo. The resultant was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 38 (15.6 g, 65%) as a white solid.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated in vacuo
  4. customThe resultant was partitioned between EtOAc and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d82195d075564c2696064b360c48585f
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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