Sodium hydride → Ethyl-alpha-bromo-p-cyanophenylacetate

HRID 22556Notes

Reaction equation

HRID 22556 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[Br:17]N1C(=O)CCC1=O>COCCOCCOC>[CH2:13]([O:12][C:10](=[O:11])[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[Br:17])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 279718Ethyl 2-(4-cyanophenyl)acetate

Product 1

HCID 19930427Ethyl-alpha-bromo-p-cyanophenylacetate

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of 1.9 g of ethyl p-cyanophenylacetate in 50 ml of diglyme is added to a slurry of 0.48 g of sodium hydride (50% oil dispersion) in 10 ml of diglyme. The reaction mixture is stirred at room temperature for 2 h, cooled to 0° and 1.75 g of N-bromosuccinimide is added portionwise. The solvent is evaporated under high vacuum and the residue is chromatographed on 50 g of silica with ether to yield ethyl-α-bromo-p-cyanophenylacetate.

Workup

  1. temperaturecooled to 0°
  2. customThe solvent is evaporated under high vacuum
  3. customthe residue is chromatographed on 50 g of silica with ether

Sources & evidence

ORD record
ord-53eb59246637417281718ac77f902392
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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