N-bromobutanimide → 2-Bromomethyl-5-iodo-benzofuran

HRID 1171218Notes

Reaction equation

HRID 1171218 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[CH:7][C:6]=2[CH:11]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:11][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 38560465-Iodo-2-methylbenzofuran

Product 1

HCID 687159772-Bromomethyl-5-iodo-benzofuranYield 49%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a carbon tetrachloride (28 mL) solution of 5-iodo-2-methylbenzofuran (500 mg, 1.94 mmol) were added N-bromosuccinimide (410 mg, 2.3 mmol) and 2,2-azobis(isobutyronitrile) (47.8 mg, 0.291 mmol). This mixture was stirred for 2 hours and 45 minutes while heating under reflux. After allowing the reaction mixture to cool on standing, the reaction mixture was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2-bromomethyl-5-iodo-benzofuran (320 mg, 49%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. temperatureto cool
  4. concentrationthe reaction mixture was concentrated under a reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d6acf06130aa40f595b3746da7821ab6
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…