Azobisisobutyronitrile → methyl 2-bromomethyl-1-naphthoate

HRID 1610233Notes

Reaction equation

HRID 1610233 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10954574HCID 10954574, compound

Product 1

HCID 11437414methyl 2-bromomethyl-1-naphthoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 2-methyl-1-naphthoate (1.277 g, 6.377 mmol), N-bromosuccinimide (1.14 g, 6.38 mmol) and 2,2′-azobis(isobutyronitrile) (10 mg) in carbon tetrachloride (10 ml) was heated under reflux for 0.5 hr. After cooling the reaction solution to room temperature, the white precipitate was removed by filtration, and the precipitate was washed with diethyl ether. The solvent of the collected filtrate was evaporated under reduced pressure to give a crude product of methyl 2-bromomethyl-1-naphthoate as a pale-yellow liquid. The obtained liquid, thiophenol (0.84 g, 7.65 mmol) and 1,8-diazabicyclo[5.4.0]-7-undecene (1.14 ml, 7.65 mmol) were stirred in acetonitrile (20 ml) overnight at room temperature. The solvent of the reaction solution was evaporated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=20/1-9/1) to give the objective substance.

Workup

  1. temperatureunder reflux for 0.5 hr
  2. customthe white precipitate was removed by filtration
  3. washthe precipitate was washed with diethyl ether
  4. customThe solvent of the collected filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1db16e8f88974679a01e053fad4d5533
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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