N-bromobutanimide → 4'-(Bromomethyl)-2-cyanobiphenyl

HRID 1708399Notes

Reaction equation

HRID 1708399 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]#[N:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylYield 59.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

7.9 g of 4'-methyl-2-cyanobiphenyl, prepared in A), are dissolved in 100 ml of carbon tetrachloride in the presence of 7.3 g of N-bromosuccinimide and 0.3 g of benzoyl peroxide. The mixture is heated to reflux for 6 hours and the crystals are filtered off; the remaining solution is concentrated under vacuum and the residue is crystallised in ether to give 6.6 g of 4'-bromomethyl-2-cyanobiphenyl in the form of crystals of melting point 115°-118° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 6 hours
  3. filtrationthe crystals are filtered off
  4. concentrationthe remaining solution is concentrated under vacuum
  5. customthe residue is crystallised in ether

Sources & evidence

ORD record
ord-f513c530a72e4d8b9b73281b68d155e3
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

Loading…