Urea → 2-Bromo-4-chlorobenzonitrile

HRID 2099307Notes

Reaction equation

HRID 2099307 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.[NH2:12]C(N)=O>ClCCl.CO>[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]#[N:12]

Participants

4

Reactant 2

HCID 1176UreaHCID 331262-Bromo-4-chlorobenzoic acid

Product 1

HCID 234985242-Bromo-4-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

588 mg of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanol and concentrated onto 364 mg of alumina on a rotary evaporator. The residue is irradiated in a microwave at 150° C. for a total of 60 min. After cooling, the residue is stirred with ethyl acetate and water, filtered, and the aqueous phase of the filtrate is separated. The organic phase is washed with a sodium hydrogen carbonate solution, dried over sodium sulfate, concentrated on a rotary evaporator and then dried under high vacuum. The product is reacted further without additional purification.

Workup

  1. concentrationconcentrated onto 364 mg of alumina on a rotary evaporator
  2. customThe residue is irradiated in a microwave at 150° C. for a total of 60 min
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customthe aqueous phase of the filtrate is separated
  6. washThe organic phase is washed with a sodium hydrogen carbonate solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated on a rotary evaporator
  9. customdried under high vacuum
  10. customThe product is reacted further without additional purification

Sources & evidence

ORD record
ord-562b46d045904eef94fade5caec544e8
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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