Iodine → HCID 603312, compound

HRID 2243466Notes

Reaction equation

HRID 2243466 reaction equation
[Mg].II.[Br:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11]Br.Cl[P:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C([Li])CCC.C(OCC)C>[Br:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][P:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 807IodineHCID 66180ChlorodiphenylphosphineHCID 769652-Bromobenzyl bromideHCID 5462224Magnesium

Product 1

HCID 603312HCID 603312, compound

Reagents, catalysts & solvents 2

HCID 178418339ButyllithiumCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Under nitrogen, magnesium (1.87 g) was placed in a 3-neck 250 ml round bottom flask along with about 60 ml of diethyl ether and a few crystals of iodine and a few drops of n-butyl lithium (2M). 1-bromo-2-(bromomethyl)benzene (17.5 g) was added to an addition funnel along with 20 ml of diethyl ether. This solution was added dropwise to the mixture. The reaction was refluxed for an additional ½ hour after dropwise addition was completed. Chlorodiphenylphosphine (11.3 ml) in 20 ml of diethyl ether was then added dropwise with vigorous stirring to the Grignard solution at a rate to maintain a reflux. When the addition was complete, the reaction was refluxed for an additional hour and then cooled to room temperature and quenched with aqueous hydrochloric acid (dropwise addition) under nitrogen. The layers were separated and the organic layer was washed with water. The mixture was then filtered, separated, and dried. The solvent was then removed to obtain 24.8 g of (2-bromobenzyl)diphenyl-phosphine.

Workup

  1. additionThis solution was added dropwise to the mixture
  2. temperatureThe reaction was refluxed for an additional ½ hour
  3. additionafter dropwise addition
  4. temperatureto maintain a reflux
  5. additionWhen the addition
  6. temperaturethe reaction was refluxed for an additional hour
  7. customquenched with aqueous hydrochloric acid (
  8. additiondropwise addition) under nitrogen
  9. customThe layers were separated
  10. washthe organic layer was washed with water
  11. filtrationThe mixture was then filtered
  12. customseparated
  13. customdried
  14. customThe solvent was then removed

Sources & evidence

ORD record
ord-be4bd20e845a4ef4930119584c18fdbb
Source dataset
uspto-grants-2010_03
Patent number
US07674937B2

Reaction notes

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