Benzoyl Peroxide → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 580640Notes

Reaction equation

HRID 580640 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:13]([C:12]1[CH:17]=[CH:18][C:19]([CH2:21][Br:1])=[CH:20][C:11]=1[O:10][CH3:9])([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (45.3 g) was added to methyl 2-methoxy-4-methylbenzoate (45.8 g) in carbon tetrachloride (~11) containing a trace of dibenzoyl peroxide. The suspension was heated under reflux until no orange colour persisted, then cooled, filtered and the filtrate evaporated to give the title compound, bp 136°-144°/7 mm. τ (CDCl3) 6.17 (3H, s), 6.13 (3H, s), 5.59 (2H, s), 2.9-3.15 (2H, m), 2.3 (1H, J=8 Hz).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux until no orange colour
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-8e24ff6199e149c8920c0c7b45749d0a
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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