Bromine → 5-(2-Bromoacetyl)-2-fluorobenzonitrile

HRID 2175806Notes

Reaction equation

HRID 2175806 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10])(=[O:3])[CH3:2].[Br:13]Br>C(Cl)Cl>[Br:13][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:12])=[C:8]([CH:11]=1)[C:9]#[N:10])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 224583893'-Cyano-4'-fluoroacetophenone

Product 1

HCID 867270445-(2-Bromoacetyl)-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-acetyl-2-fluorobenzonitrile (20.0 g, 0.123 mol) in 500 mL of DCM was heated to reflux for 2 h, and then a solution of bromine in 300 mL DCM was added dropwise into the boiling mixture. The reaction mixture was heated to reflux and stirred under N2 protection overnight. The reaction mixture was washed with water and extracted with DCM. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuum. The residue was purified via silica gel column chromatography to give 5-(bromoacetyl)-2-fluorobenzonitrile.

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. washThe reaction mixture was washed with water
  5. extractionextracted with DCM
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuum
  9. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-977ae9cde35e40ce9a79f6064d05954f
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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