N-bromobutanimide → Methyl 4-(bromomethyl)-3-methoxybenzoate

HRID 1009914Notes

Reaction equation

HRID 1009914 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].[Br:14]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(OCC)(=O)C>[Br:14][CH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Product 1

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateYield 92%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-methoxy-4-methylbenzoate (10.0 g, 55.5 mmol), N-bromosuccinimide (10.7 g, 60.9 mmol), 2,2′-azobis(isobutyronitrile) (1.6 mg) and ethyl acetate (200 ml) was heated under reflux overnight. The solvent was evaporated under reduced pressure, and hexane was added to the residue. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (9:1-7:3, v/v) to give the title compound (12.8 g, 92%) as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe solvent was evaporated under reduced pressure, and hexane
  4. additionwas added to the residue
  5. filtrationThe precipitate was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washeluted with hexane-ethyl acetate (9:1-7:3

Sources & evidence

ORD record
ord-c3569091b41240a49dd4c372d9175bd0
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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