N-bromobutanimide → 1-Bromo-2-(bromomethyl)naphthalene

HRID 2081178Notes

Reaction equation

HRID 2081178 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][Br:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 757541-Bromo-2-methylnaphthalene

Product 1

HCID 378281-Bromo-2-(bromomethyl)naphthaleneYield 42.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-Bromo-2-methyl naphthalene (25 g), N-bromosuccinimide (24.2 g), carbon tetrachloride (250 mL) and a catalytic amount of azo(bis)isobutylnitrile were refluxed 40 hours under a nitrogen atmosphere. The reaction was cooled to room temperature and volatile materials were removed in vacuo on a rotary evaporator. the residue was treated with hot hexane (steam bath, about 2×250 mL). The hexane solution was decanted and cooled in ice. The product was collected on a Buchner funnel and air dried to give 14.5 g of 1-bromo-2-bromomethylnaphthalene as white crystals.

Workup

  1. customvolatile materials were removed in vacuo on a rotary evaporator
  2. additionthe residue was treated with hot hexane (steam bath, about 2×250 mL)
  3. customThe hexane solution was decanted
  4. temperaturecooled in ice
  5. customThe product was collected on a Buchner funnel and air
  6. customdried

Sources & evidence

ORD record
ord-a7a4a106df14480a99c64818f921cf13
Source dataset
uspto-grants-1993_02
Patent number
US05183825

Reaction notes

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