N-bromobutanimide → Methyl 4-bromomethyl-3-cyanobenzoate

HRID 1839446

Reaction equation

HRID 1839446 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.[W]>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][Br:21])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11819538Methyl 3-cyano-4-methylbenzoate

Product 1

HCID 23450362Methyl 4-bromomethyl-3-cyanobenzoateYield 48.2%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 3-cyano-4-methylbenzoate (1.78 g, 9.79 mmol) and NBS (1.92 g, 10.8 mmol) in CCl4 (150 mL) was irradiated with a 150W tungsten lamp at 50 C. for 2 h. The reaction was cooled, filtered, and concentrated. The residue was chromatographed (250 g silica, 10% EtOAc/hexanes to 15% EtOAc/hexanes) to give the title compound (1.20 g, 48%); IR(CHCl3: 1291, 1302, 1439, 1728 cm−1; NMR(300 MHz, CDCl3): 4.01 (s, 3H); 4.67 (s, 3H); 7.66 (d, 1H, J=8.1 Hz); 8.24 (d, 1H, J=8.7 Hz); 8.34 (s, 1H); MS(FD): 253.0.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was chromatographed (250 g silica, 10% EtOAc/hexanes to 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1937ec6ff2d3445fa266782360fae036
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Linked notes

Loading…