Methyl 3-bromo-4-ethylbenzoate → HCID 57935767, compound

HRID 1434576Notes

Reaction equation

HRID 1434576 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[Cu][C:15]#[N:16]>CN1C(=O)CCC1.O>[C:15]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])#[N:16]

Participants

5

Reactant 2

HCID 13877473Methyl 3-bromo-4-ethylbenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 57935767HCID 57935767, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 3-bromo-4-ethyl-benzoate (D44) (5 g) in NMP (180 mL) was treated with copper (I) cyanide (3.69 g). The mixture was then heated at reflux for 5 h, under argon. After cooling to 20° C. the reaction mixture was diluted with water, then filtered through kieselguhr, washing well with water and EtOAc. The organic layer was washed with water, brine and dried over MgSO4. The solvent was evaporated to dryness in vacuo and the residue was purified by chromatography on silica eluting with EtOAc-Hexane (1:9) to give the title compound (1.9 g) 1H NMR (CDCl3) δ 1.33 (3H, t), 2.94 (2H, q), 3.94 (3H, s), 7.43 (1H, d), 8.17 (1H, dd), 8.28 (1H, d).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 5 h, under argon
  3. filtrationfiltered through kieselguhr
  4. washwashing well with water and EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated to dryness in vacuo
  8. customthe residue was purified by chromatography on silica eluting with EtOAc-Hexane (1:9)

Sources & evidence

ORD record
ord-c03fb10769df4fdc886e65121664c9c9
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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