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

HRID 618749Notes

Reaction equation

HRID 618749 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-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 CH2Cl 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 CH2Cl 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-77560c0366c446ad8eb8f75a9f146e5a
Source dataset
uspto-grants-1999_09
Patent number
US05955487

Reaction notes

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