Benzoyl Peroxide → methyl 2-bromomethyl-1-naphthoate

HRID 2177796Notes

Reaction equation

HRID 2177796 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]([O:22][CH3:23])=[O:21].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(OCC)(=O)C>C(#N)C>[Br:1][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 10954574HCID 10954574, compound

Product 1

HCID 11437414methyl 2-bromomethyl-1-naphthoateYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (0.748 g) was added to a solution of methyl 2-methylnapthalene-1-carboxylate (0.7 g) in acetonitrile (30 ml) and the mixture was heated to reflux. Benzoyl peroxide (0.093 g) was added and the reaction mixture was heated at reflux for 4 hours. After cooling, ethyl acetate was added and the solution was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM and pentane with a gradient of 7.5-25% to give methyl 2-bromomethylnaphthalene-1-carboxylate (0.529 g) as a yellow solid.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 4 hours
  4. temperatureAfter cooling
  5. washthe solution was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of DCM and pentane with a gradient of 7.5-25%

Sources & evidence

ORD record
ord-0a3d5da55cae4d8da9d721fd1a32ed94
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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