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

HRID 2427497Notes

Reaction equation

HRID 2427497 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[CH3:11].[Br:13]N1C(=O)CCC1=O.C(OO[C:31](=[O:38])C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:38][CH3:31])=[CH:6][C:5]=1[CH2:11][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2782181Methyl 4-fluoro-2-methylbenzoate

Product 1

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Fluoro-2-methyl-benzoic acid methyl ester (600 mg, 3.6 mmol), N-bromosuccinimide (635 mg, 3.6 mmol) and benzoyl peroxide (43 mg, 1.79 mmol) in CCl4 (15 mL) was stirred at 90° C. for 3 hours. The reaction was cooled to room temperature, filtered, washed with CCl4 and the solvent was removed under reduced pressure to provide a white solid. 1H NMR (300 MHz, CDCl3): δ 8.01 (d, 1H), 6.99 (d, 1H), 6.88 (dd, 1H), 4.98 (s, 2H), 3.93 (s, 3H), 3.89 (s, 3H).

Workup

  1. filtrationfiltered
  2. washwashed with CCl4
  3. customthe solvent was removed under reduced pressure
  4. customto provide a white solid

Sources & evidence

ORD record
ord-585d8bb5c5c04e44911c0a114fddbf7a
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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