N-bromobutanimide → Methyl 3-bromo-2-(bromomethyl)benzoate

HRID 908290Notes

Reaction equation

HRID 908290 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[C:3]([CH2:12][Br:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoateYield 100.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 3-bromo-2-methylbenzoate (7.45 g, 32.5 mmol) was dissolved in CCl4 (94 ml) and N-bromosuccinimide (6.67 g, 37.5 mmol) and benzoyl peroxide (0.38 g, 1.6 mmol) were added. The reaction was heated to 75 C-85 C, stirred for 3 hours and 45 minutes, cooled to room temperature, and filtered. The filtrate was concentrated and purified on SiO2 (Biotage instrument; 0%->20% EtOAc/hexanes) to give methyl 3-bromo-2-(bromomethyl)benzoate (10.07 g, 100%).

Workup

  1. temperatureThe reaction was heated to 75 C-85 C
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified on SiO2 (Biotage instrument; 0%->20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2995c082a75e40908303e7524c29b44e
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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