N-bromobutanimide → Methyl 4-Bromo-3-(bromomethyl)benzoate

HRID 63860

Reaction equation

HRID 63860 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][Br:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3294148Methyl 4-bromo-3-methylbenzoate

Product 1

HCID 11460987Methyl 4-Bromo-3-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Into a 500-mL round-bottom flask, was placed a solution of methyl 4-bromo-3-methylbenzoate (10 g, 43.65 mmol, 1.00 equiv) in CCl4 (150 ml), NBS (8.12 g, 45.62 mmol, 1.05 equiv). The resulting solution was heated to reflux overnight under 100 w incandescent bulb. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 6 g (47%) of methyl 4-bromo-3-(bromomethyl)benzoate as a off-white solid.

Workup

  1. customInto a 500-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight under 100 w incandescent bulb
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 6 g (47%) of methyl 4-bromo-3-(bromomethyl)benzoate as a off-white solid

Sources & evidence

ORD record
ord-23f365dc9e894a0e8ff6efca2648a828
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Linked notes

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