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

HRID 975283Notes

Reaction equation

HRID 975283 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(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[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 59.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5.59 g of 4'-methyl-2-cyanobiphenyl, 29 mmol of N-bromosuccinimide, 0.9 mmol of benzoylperoxide and 500 mL of carbon tetrachloride was refluxed for 3 hours. After cooling to room temperature, the resulting suspension was filtered and then concentrated in vacuo to provide the crude 4'-bromomethyl-2-cyanobiphenyl. The product was recrystallized from ether to yield 4.7 g of product; m.p. 114.5°-120.0°. NMR (200 MHz, CDCl3)δ7.8214 7.37 (m, 8H); 4.50 (s, 2H).

Workup

  1. filtrationthe resulting suspension was filtered
  2. concentrationconcentrated in vacuo
  3. customto provide the crude 4'-bromomethyl-2-cyanobiphenyl
  4. customThe product was recrystallized from ether

Sources & evidence

ORD record
ord-9b43a00273f842f7958bb4a5c558f90b
Source dataset
uspto-grants-1997_03
Patent number
US05608075

Reaction notes

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