Iodine → 1-Bromo-3-cyclopropylbenzene

HRID 733193

Reaction equation

HRID 733193 reaction equation
II.I[CH2:4]I.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[CH2:11]>C1(C)C=CC=CC=1.[Cu]>[Br:6][C:7]1[CH:8]=[C:9]([CH:10]2[CH2:4][CH2:11]2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 807IodineHCID 6346DiiodomethaneHCID 748703-Bromostyrene

Product 1

HCID 32826721-Bromo-3-cyclopropylbenzeneYield 10.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

Iodine (0.335 g, 1.32 mmol), diiodomethane (4.3 mL, 53.0 mmol) and 3-bromostyrene (5 g, 26.4 mmol) were added successively to a suspension of copper (7.5 g, 118.8 mmol) in toluene (50 mL). The mixture was refluxed for 140 h, then filtered and concentrated in vacuo. The residue was distilled under reduced pressure to afford 3-bromo-1-cyclopropylbenzene (0.55 g, 10%) as a colorless oil.

Workup

  1. temperatureThe mixture was refluxed for 140 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-92a3c950b0de4d5d9a1452cdff580344
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Linked notes

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