N-bromobutanimide → Methyl 5-(bromomethyl)-2-methoxybenzoate

HRID 2202592Notes

Reaction equation

HRID 2202592 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[Br:14]N1C(=O)CCC1=O>C(#N)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10241396Methyl 2-methoxy-5-methylbenzoate

Product 1

HCID 19744340Methyl 5-(bromomethyl)-2-methoxybenzoateYield 44%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere, methyl 2-methoxy-5-methylbenzoate (901 mg, 5 mmol) was dissolved in acetonitrile, and N-bromosuccinimide (890 mg, 5 mmol) and benzoyl peroxide (24 mg, 0.1 mmol) were added thereto. The mixture was refluxed for one hour. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature, and the solvent was distilled off. Thereafter, the residue was dissolved in ethyl acetate. The organic layer was washed with water 3 times and then with a saturated saline solution, and dried over magnesium sulfate. The solvent was distilled off, and then the resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1) to give the title compound (570 mg, 44.0%) as an oily substance.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. distillationthe solvent was distilled off
  3. dissolutionThereafter, the residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water 3 times
  5. dry with materialwith a saturated saline solution, and dried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1)

Sources & evidence

ORD record
ord-363618aa9b0c4c0fa230acbfc2a2d92c
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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