Water → HCID 12074416, compound

HRID 1265971Notes

Reaction equation

HRID 1265971 reaction equation
[Br:1][C:2](=[CH2:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[OH-].[Na+].O.[CH:15]([Br:18])(Br)[Br:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C:2]2([Br:1])[CH2:11][C:15]2([Br:18])[Br:16])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5558BromoformHCID 14798Sodium HydroxideHCID 100368921-(2-Bromoprop-2-en-1-yl)-4-chlorobenzene

Product 1

HCID 12074416HCID 12074416, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
58.5 °C

Procedure

To a solution of 11.4 g (0.0494 mol) of 1-(2-bromo-allyl)-4-chloro-benzene in 20 ml of bromoform was added 0.686 g (0.00213 mol) tetrabutylammonium bromide. After heating to 58.5° C. for an hour, 10.7 ml (0.0494 mol) of 50% aqueous sodium hydroxide was added. This was repeated seven times over two days. After cooling to room temperature there was added hexanes and water. This mixture was gravity filtered through qualitative fluted filter paper. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo. This residue was purified by column chromatography with hexanes to give 2.3 g of 2-(4-chlorophenylmethyl)-1,1,2-tribromocyclopropane.

Workup

  1. customover two days
  2. temperatureAfter cooling to room temperature there
  3. filtrationfiltered through qualitative fluted filter paper
  4. customThe resulting mixture was transferred to a separatory funnel
  5. customthe phases were separated
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo
  9. customThis residue was purified by column chromatography with hexanes

Sources & evidence

ORD record
ord-d06abb4d46ac4875ae15b7338d85d734
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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