Water → Methyl 2-(bromomethyl)-4-methoxybenzoate

HRID 705432Notes

Reaction equation

HRID 705432 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 13257269Methyl 4-methoxy-2-methylbenzoate

Product 1

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoateYield 144.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of methyl 4-methoxy-2-methylbenzoate (1 g, 5.6 mmol) in CCl4 (25 mL) was added dropwise N-bromosuccinimide (1.1 g, 6.2 mmol) previously dissolved in CCl4 (5 mL) and a catalytic amount of benzoyl peroxide. The mixture was refluxed for 2 hours, cooled to room temperature and poured onto iced water. The aqueous mixture was extracted with DCM (3×), and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to provide 2.1 g of the titled product as light yellow solid (˜100% yield): [M+H+] m/z 260.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionThe aqueous mixture was extracted with DCM (3×)
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e795ad648eb4783bb88525a6e9df91e
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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