Azobisisobutyronitrile → 1-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene

HRID 1875047Notes

Reaction equation

HRID 1875047 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[C:6]([F:19])[C:5]([CH3:20])=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:20][C:5]1[C:6]([F:19])=[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 684882771-[(6-Chloro-2-fluoro-3-methylphenyl)oxy]naphthalene

Product 1

HCID 684855581-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthaleneYield 45.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-[(6-chloro-2-fluoro-3-methylphenyl)oxy]naphthalene (1.69 g, 5.89 mmol) in carbon tetrachloride (20 mL) was added N-bromosuccinimide (1.154 g, 6.48 mmol) and AIBN (0.048 g, 0.295 mmol). The mixture was heated at reflux overnight. The reaction mixture was filtered through Celite and the solvent was evaporated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the desired product (0.98 g, 45.5%) as a light yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.43-8.51 (m, 1H), 7.84-7.92 (m, 1H), 7.53-7.64 (m, 3H), 7.23-7.34 (m, 3H), 6.50 (d, 1H), 4.50 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-aedcfd401bbe4b488797dda86d99bc54
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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