N-bromobutanimide → Ethyl 2-bromomethyl-6-methoxybenzoate

HRID 2188012Notes

Reaction equation

HRID 2188012 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH3:13])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([CH2:11][Br:15])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH3:13])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Product 1

HCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoateYield 85%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methoxy-6-methylbenzoic acid ethyl ester (500 mg, 2.67 mmol), N-bromosuccinimide (483.8 mg, 2.72 mmol) and 2,2′-azobis(2-methyl-propionitrile) (30.2 mg, 0.123 mmol) in carbon tetrachloride (10 ml) were heated to reflux. After 18 hours, the reaction mixture was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane (100 ml) and washed with water (2×50 ml). The organic layer was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue (702 mg) was purified by column chromatography using a mixture of hexanes/dichloromethane (1:1) as eluent, which afforded 573 mg (85%) of 6-bromomethyl-2-methoxy-benzoic acid ethyl ester as an oil.

Workup

  1. customthe reaction mixture was evaporated to dryness in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. washwashed with water (2×50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue (702 mg) was purified by column chromatography
  8. additiona mixture of hexanes/dichloromethane (1:1) as eluent

Sources & evidence

ORD record
ord-cc465524f3c54e1ab1319e52cd5fbc82
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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