Triphenylphosphine → HCID 13375186, compound

HRID 236657Notes

Reaction equation

HRID 236657 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH3:22][C@@:23]1([CH2:37][CH2:38]O)[CH2:32][CH2:31][C:30]2[C:25](=[C:26]([CH3:36])[C:27]([CH3:35])=[C:28]([OH:34])[C:29]=2[CH3:33])[O:24]1>C(Cl)Cl>[CH3:22][C@@:23]1([CH2:37][CH2:38][Br:20])[CH2:32][CH2:31][C:30]2[C:25](=[C:26]([CH3:36])[C:27]([CH3:35])=[C:28]([OH:34])[C:29]=2[CH3:33])[O:24]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 642448HCID 642448, compound

Product 1

HCID 13375186HCID 13375186, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.5 g of triphenylphosphine were dissolved in 100 ml of anhydrous methylene chloride, 3.4 g of bromine were added dropwise, the reaction mixture was stirred for 30 minutes at room temperature, 5 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-hydroxyethyl)-chroman were added, and the mixture was refluxed for one hour and then poured onto sodium carbonate solution. The aqueous phase was extracted with methylene chloride, the combined organic phases were washed with sodium chloride solution, dried and evaporated down, and the residue was recrystallized from methanol. 5.3 g of (S)-2,5,7,8-tetramethyl-6-hydroxy-2-(2-bromoethyl)-chroman were obtained. [α]D20 =-15 (c=2, MeOH), mp.=120° C.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. additionpoured onto sodium carbonate solution
  3. extractionThe aqueous phase was extracted with methylene chloride
  4. washthe combined organic phases were washed with sodium chloride solution
  5. customdried
  6. customevaporated down
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-cd71b2a8e08449f9a440f0c13191920a
Source dataset
uspto-grants-1987_02
Patent number
US04645845

Reaction notes

Loading…