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

HRID 906814Notes

Reaction equation

HRID 906814 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-1517f3113a9e47e1bedeb190e1609fe0
Source dataset
uspto-grants-2011_09
Patent number
US08012997B2

Reaction notes

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