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

HRID 2103577Notes

Reaction equation

HRID 2103577 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-a57000965ae241c29b2250f4e434e5c2
Source dataset
uspto-grants-2009_08
Patent number
US07576104B2

Reaction notes

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