Benzoyl Peroxide → 1-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl ester

HRID 735893Notes

Reaction equation

HRID 735893 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21973653Methyl 4-methylnaphthalene-1-carboxylate

Product 1

HCID 103338131-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 4-methyl-1-naphthoate (22.5 g, 0.112 mol) in CCl4 (500 mL) was added NBS (22 g, 0.123 mol) and benzoylperoxide (10% w/w). The reaction mixture was allowed to reflux at 80° C. for 7 h. The reaction mixture was cooled to rt and filtered off. The solid and concentrated under vacuum and the obtained crude product (30 g) was used for further reaction.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered off
  3. concentrationThe solid and concentrated under vacuum

Sources & evidence

ORD record
ord-e0130883a69e4f88bebd96f485c322ab
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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