Ammonia → Methyl 4-bromo-2-cyanobenzoate

HRID 1804134Notes

Reaction equation

HRID 1804134 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](I)[CH:3]=1.[Cu](C#N)[C:14]#[N:15].[Cl-].[NH4+].N>C(OCC)(=O)C.O.CN1CCCC1=O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:14]#[N:15])[CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 58484707Methyl 4-bromo-2-iodobenzoateHCID 178418260HCID 178418260, compound

Product 1

HCID 58484706Methyl 4-bromo-2-cyanobenzoateYield 99.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 4-bromo-2-iodobenzoate (3.52 g) described in Preparation Example 190 were added copper cyanide (1.16 g) and N-methylpyrrolidone (21 mL) and the mixture was stirred at 60° C. for 1 hr. Under cooling with water, ethyl acetate, saturated aqueous ammonium chloride solution and aqueous ammonia were added and the mixture was extracted with ethyl acetate. The organic layer was washed once with saturated aqueous ammonium chloride solution and aqueous ammonia, once with saturated aqueous ammonium chloride solution and once with saturated brine, and dried over sodium sulfate. The solvent was evaporated to give the title compound (2.39 g).

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed once with saturated aqueous ammonium chloride solution and aqueous ammonia, once with saturated aqueous ammonium chloride solution and once with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5b880029ae2d4423a8623c422b4880ce
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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