Hydrochloric Acid → HCID 14548449, compound

HRID 1904509Notes

Reaction equation

HRID 1904509 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([CH3:10])[CH:6]=[C:7]([CH3:9])[CH:8]=1.Cl[P:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>O1CCCC1>[CH3:9][C:7]1[CH:8]=[C:3]([P:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=[C:5]([CH3:10])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66180ChlorodiphenylphosphineHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 5462224Magnesium

Product 1

HCID 14548449HCID 14548449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 3-neck 1 liter flask equipped with blade stirrer, nitrogen inlet, Claissen adaptor, condenser, drying tube and constant pressure dropping funnel, was placed 6.67 g (0.274 g atoms) of magnesium turnings. Under a nitrogen flow, the glassware was dried with heating via a heat gun. To the magnesium was added a portion of a solution of 55.5 g (0.30 mol) of 5-bromo-m-xylene in 150 ml dry THF (tetrahydrofuran). Reaction was initiated with external heating and the balance of the solution was added dropwise over approximately 30 min, maintaining gentle reflux. the mixture was then stirred for another 1 hr after which a solution of 41.3 g (0.188 mol) of chlorodiphenyl-phosphine in 150 ml of dry THF was added over approximately 10 min. The mixture was then heated at reflux for 2 hr, cooled and poured into ice. The mixture was neutralized with concentrated HCl and nitrogen was bubbled through the mixture overnight. The organic layer was taken up in methylene chloride and separated from the aqueous layer. Concentrating the organic layer afforded an oil which crystallized on standing. After triturating with an equal volume of methanol, the solid was collected and recrystallized from methanol. The yield of 3,5-dimethylphenyldiphenylphosphine was 37.5 g (68.7% of theory); mp=67°-9° C.

Workup

  1. customIn a 3-neck 1 liter flask equipped with blade stirrer, nitrogen inlet
  2. customClaissen adaptor, condenser, drying tube
  3. customUnder a nitrogen flow, the glassware was dried
  4. temperaturewith heating via a heat gun
  5. customReaction
  6. temperaturewith external heating
  7. additionthe balance of the solution was added dropwise over approximately 30 min
  8. temperaturemaintaining gentle reflux
  9. additionwas added over approximately 10 min
  10. temperatureThe mixture was then heated
  11. temperatureat reflux for 2 hr
  12. temperaturecooled
  13. additionpoured into ice
  14. customwas bubbled through the mixture overnight
  15. customseparated from the aqueous layer
  16. concentrationConcentrating the organic layer
  17. customafforded an oil which
  18. customcrystallized
  19. customAfter triturating with an equal volume of methanol
  20. customthe solid was collected
  21. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8ec9f93e9b2d4d3fb9b4da76a0db253e
Source dataset
uspto-grants-1989_06
Patent number
US04837394

Reaction notes

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