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

HRID 10059Notes

Reaction equation

HRID 10059 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(#N)C>[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

4

Reactant 2

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

Product 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoateYield 107.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-bromo-2-methylbenzoate (17.0 g, 74.22 mmol) and N-bromosuccinimide (15.85 g, 89.06 mmol) in acetonitrile (200 mL) was heated under gently refluxing for 17 hours while a 200 W bulb situated 2 cm away was shining on the reaction flask. The mixture was cooled to room temperature and solvent was removed. The residue was dissolved in ethyl acetate (200 mL) and washed with water (3×80 mL), brine (80 mL) and dried (MgSO4). Solvent was removed to give methyl 3-bromo-2-bromomethylbenzoate (24.5 g, 97% by HPLC): 1H NMR (CDCl3) δ 7.90–7.86 (dd, J=1.0 and 7.9 Hz, 1H), 7.78–7.74 (dd, J=1.2 and 8.2 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 5.12 (s, 2H), 3.95 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder gently refluxing for 17 hours while a 200 W bulb
  3. customsolvent was removed
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with water (3×80 mL), brine (80 mL)
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed

Sources & evidence

ORD record
ord-b650c99db20d4ba6b8fdcb17dc1d1211
Source dataset
uspto-grants-2006_08
Patent number
US07091353B2

Reaction notes

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