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

HRID 1434875Notes

Reaction equation

HRID 1434875 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Br:14]Br>C(Cl)(Cl)(Cl)Cl.[W]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH2:13][Br:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoateYield 96.1%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a refluxing mixture of methyl 2-methoxy-4-methyl-benzoate (21.625 g, 120 mmol) in CCl4 (240 mL) was added dropwise a solution of bromine (6.19 mL, 120 mmol) in CCl4 (75 mL) over 1.5 h. During the bromine addition the reaction was irradiated with a 250 W tungsten lamp. After the addition, the reaction was refluxed for 15 min and concentrated, and vacuum pumped to give methyl 2-methoxy-4-(bromomethyl)benzoate as an oil (29.864 g, 96%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was refluxed for 15 min
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f6cdaccee7614804b9bebd95aae5ea66
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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