N-bromobutanimide → 4-(3-Cyano-2-thienyl)benzyl bromide

HRID 1708419Notes

Reaction equation

HRID 1708419 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:13]([C:12]1[CH:11]=[CH:10][S:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][Br:15])=[CH:7][CH:6]=1)#[N:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 200928362-(4-Methylphenyl)thiophene-3-carbonitrile

Product 1

HCID 200928574-(3-Cyano-2-thienyl)benzyl bromideYield 40.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

24.5 g of 2-(4-methylphenyl)-3-cyanothiophene, prepared in E), are dissolved in 200 ml of carbon tetrachloride. 21.9 g of N-bromosuccinimide are added, as well as 0.1 g of benzoyl peroxide. The mixture is heated to reflux for 24 hours. The crystals of succinimide are filtered off and the solvent is evaporated off under vacuum. The residue is taken up in a mixture of hexane and ethyl acetate and the solution is kept in a freezer for 24 hours. The crystals formed are drained to give 14 g of 4-(3-cyano-2-thienyl)benzyl bromide in the form of crystals of melting point 80° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe crystals of succinimide are filtered off
  4. customthe solvent is evaporated off under vacuum
  5. additionThe residue is taken up in a mixture of hexane and ethyl acetate
  6. customThe crystals formed

Sources & evidence

ORD record
ord-ed3c5c127f314628911976e96671415d
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

Loading…