Hydrochloric Acid → HCID 178527027, compound

HRID 556181Notes

Reaction equation

HRID 556181 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[P:21]([O-:28])(OCC)OCC.Cl>C1COCC1.C1(C)C=CC=CC=1>[C:9]1([C:6]2[CH:5]=[CH:17][CH:16]=[CH:15][CH:20]=2)[CH:14]=[CH:13][C:12]([PH:21](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:11][CH:10]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 71014-BromobiphenylHCID 78391,2-DibromoethaneHCID 3780918DiethylphosphiteHCID 5462224Magnesium

Product 1

HCID 178527027HCID 178527027, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, a solution of magnesium (2.60 g, 1.0 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in THF (20 mL) was stirred at room temperature for 30 min. A solution of 4-bromobiphenyl (25 g, 0.107 moL) in THF (20 mL) was added at 35° C. and the mixture was stirred at 40° C. for 1 hr. and then stirred at 5° C. for 30 min. A solution of diethyl phosphite (7.39 g, 0.5 equivalent) in THF (10 mL) was added at 5° C., and the mixture was stirred at 5° C. for 2 hrs. Toluene (60 mL) was added at 3° C. and 3M-HCl (30 mL) was added. The mixture was stirred at room temperature for 30 min. THF (50 mL) was added, and the reaction mixture was partitioned. The organic layer was washed with 5% aqueous NaCl solution (10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether to give the title compound (12.47 g, white crystals). yield 65.8%.

Workup

  1. stirringand then stirred at 5° C. for 30 min
  2. stirringthe mixture was stirred at 5° C. for 2 hrs
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customthe reaction mixture was partitioned
  5. washThe organic layer was washed with 5% aqueous NaCl solution (10 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered by gravity
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ca28e6454cc74b6dbd3870431df0c34f
Source dataset
uspto-grants-2011_11
Patent number
US08053604B2

Reaction notes

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