Bromine → 5-Bromo-6-methoxy-naphthalene-2-carbonitrile

HRID 1357284Notes

Reaction equation

HRID 1357284 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]#[N:16])[CH:9]=[CH:8]2>CC(O)=O>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([C:15]#[N:16])=[CH:11]2

Participants

4

Reactant 2

HCID 24408BromineHCID 3491736-Methoxynaphthalene-2-carbonitrile

Product 1

HCID 185053355-Bromo-6-methoxy-naphthalene-2-carbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (7.0 mL, 0.137 mol) in 100 mL of glacial HOAc was added under nitrogen dropwise over 4 h to a solution of 6-methoxy-naphthalene-2-carbonitrile (25.02 g, 0.137 mol) in 700 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature overnight. The solid that formed was collected by filtration, rinsed with glacial HOAc and dried under reduced pressure to give 5-bromo-6-methoxy-naphthalene-2-carbonitrile (31.35 g, 88%) as a white solid, mp 177-178° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solid that formed
  3. filtrationwas collected by filtration
  4. washrinsed with glacial HOAc
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-74ae69ad48b24a59abd662eb5ca083ec
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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