Urea → 2-Bromo-4-chlorobenzonitrile

HRID 1011212Notes

Reaction equation

HRID 1011212 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 (2.5 mmol) of 2-bromo-4-chlorobenzoic acid and 300 mg of urea are dissolved in dichloromethane/methanol and concentrated onto 364 mg of alumina (neutral) on a rotary evaporator. The residue is microwaved 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 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 (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification.

Workup

  1. concentrationconcentrated onto 364 mg of alumina (neutral) on a rotary evaporator
  2. customThe residue is microwaved at 150° C. for a total of 60 min
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customthe aqueous phase 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 (383 mg, 80% pure, 57% of theory.) is reacted further without additional purification

Sources & evidence

ORD record
ord-55b556c01c164b92bc29ab73a7a4ba3a
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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