N-bromobutanimide → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 1741834Notes

Reaction equation

HRID 1741834 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]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoateYield 29.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2-methoxy-4-methylbenzoate (6.95 g), N-bromosuccinimide (8.24 g) and catalytic amount of benzoyl peroxide (20 mg) in carbon tetrachloride (100 ml) was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (85:15) to give methyl 4-bromomethyl-2methoxybenzoate (2.92 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed on silica gel column
  6. washeluting with a mixture of n-hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-7a57622c9d984098a886b2963bfe7aa6
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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