Methyl 2-bromo-4-carbamoylbenzoate → Methyl 2-bromo-4-cyanobenzoate

HRID 1037041Notes

Reaction equation

HRID 1037041 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12](=O)[NH2:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 1

HCID 86685485Methyl 2-bromo-4-carbamoylbenzoate

Product 1

HCID 23076848Methyl 2-bromo-4-cyanobenzoateYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-bromo-4-carbamoylbenzoate (1.3 g, 5.06 mmol) in dry DMF (20 mL) was added (CNCl)3 (1.85 g, 10.12 mmol) at rt and then stirred at rt for 3 h. The reaction mixture was quenched with water and extracted with EA (100 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give crude methyl 2-bromo-4-cyanobenzoate as a white solid (1.1 g). It was used without further purification. 1H NMR (400 MHz, CDCl3): δ 8.36 (s, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 3.90 (s, 3H) ppm.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EA (100 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5f7540c8a03401ca4df9f9204b32c56
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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