N-bromobutanimide → 2-(Bromomethyl)-1-chloro-4-iodobenzene

HRID 1169874Notes

Reaction equation

HRID 1169874 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:9][C:3]1[CH:4]=[C:5]([I:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 42009962-Chloro-5-iodotoluene

Product 1

HCID 117390382-(Bromomethyl)-1-chloro-4-iodobenzeneYield 55%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-chloro-5-iodo-toluene (0.5 g, 1.98 mmol), N-bromosuccinimide (0.422 g, 2.35 mmol) and benzoyl peroxide (21.5 mg, 0.089 mmol) in dry CCl4 (5 mL) was stirred and heated to reflux for 3 h. After cooling, the mixture-was filtered, and the red filtrate was washed with a saturated solution of sodium thiosulfate (2×10 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether), to give 60 as a white solid (361 mg, 55%). 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=2.4 Hz, 1H), 7.56 (dd, J=8.7, 2.1 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 4.49 (s, 2H). MS (m/e) (positive FAB) 332.1 (M+H)+, m.p. 94-95° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe mixture-was filtered
  5. washthe red filtrate was washed with a saturated solution of sodium thiosulfate (2×10 mL)
  6. washThe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (petroleum ether)

Sources & evidence

ORD record
ord-f299178d776541c5a4c6e0eed6c6f40e
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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