N-bromobutanimide → 6-Bromomethyl-2(2'-cyanophenyl)-naphthalene

HRID 53827Notes

Reaction equation

HRID 53827 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19])[CH:6]=[CH:5]2.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 218480566-Methyl-2-(2'-cyanophenyl)-naphthalene

Product 1

HCID 218480626-Bromomethyl-2(2'-cyanophenyl)-naphthalene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6.30 g of 6 g of 6-methyl-2-(2'-cyanophenyl)-naphthalene, 4.60 g of N-bromosuccinimide and 0.085 g of azoisobutyronitrile in 70 ml of carbon tetrachloride is heated at 110° for 4 hours. The cooled reaction mixture is extracted twice with 45 ml of 2N sodium hydroxide solution each time. The aqueous phases are then extracted with 50 ml of CH2Cl2 in each case. The combined organic phases are dried over MgSO4. After removing the solvent in vacuo, the crude product is recrystallised from toluene/hexane and yields 6-bromomethyl-2(2'-cyanophenyl)-naphthalene, m.p. 171°-172°.

Workup

  1. temperatureis heated at 110° for 4 hours
  2. customThe cooled reaction mixture
  3. extractionis extracted twice with 45 ml of 2N sodium hydroxide solution each time
  4. extractionThe aqueous phases are then extracted with 50 ml of CH2Cl2 in each case
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. customAfter removing the solvent in vacuo
  7. customthe crude product is recrystallised from toluene/hexane

Sources & evidence

ORD record
ord-29ffdc87a0eb4c10b97df8e56f2bddfe
Source dataset
uspto-grants-1997_04
Patent number
US05620998

Reaction notes

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