Hydrochloric Acid → HCID 178527026, compound

HRID 1983841Notes

Reaction equation

HRID 1983841 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.[P:19]([O-:26])(OCC)OCC.Cl>O1CCCC1.C1(C)C=CC=CC=1.O>[C:10]1([PH:19](=[O:26])[C:18]2[C:5]3[C:6](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:11]=[CH:10][CH:9]=2)[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:9]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 78391,2-DibromoethaneHCID 113722-BromonaphthaleneHCID 3780918DiethylphosphiteHCID 5462224Magnesium

Product 1

HCID 178527026HCID 178527026, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, a solution of magnesium (2.94 g, 2.00 equivalents), a slight amount of iodine and 1,2-dibromoethane in tetrahydrofuran (60 mL) was stirred at a room temperature for 1 hour. After addition of a solution of 2-bromonaphthalene (25.00 g, 2.00 equivalent) in tetrahydrofuran (20 mL) at 27° C., the mixture was stirred at 40° C. for 45 minutes. Then, after addition of a solution of diethyl phosphite (9.77 g, 0.06 mol) in tetrahydrofuran (10 mL) at −9° C., the mixture was stirred at 2° C. for 3 hours. Further, water (20 mL) was added thereto at −5° C., followed by further addition of toluene (60 mL) and 6M-HCl (20 mL). The resulting mixture was separated into layers, and the organic layer obtained was successively washed with an aqueous 5% NaHCO3 solution and an aqueous 5% NaCl solution. The organic layer was dried over dehydrated magnesium sulfate and then spontaneously filtered, and the filtrate obtained was concentrated under reduced pressure. The residue was recrystallized from isopropyl ether/n-hexane and dried (under reduced pressure at 40° C.) to obtain the titled compound (9.621 g, white powder). The yield was 53.0%.

Workup

  1. stirringthe mixture was stirred at 2° C. for 3 hours
  2. customThe resulting mixture was separated into layers
  3. customthe organic layer obtained
  4. washwas successively washed with an aqueous 5% NaHCO3 solution
  5. dry with materialThe organic layer was dried over dehydrated magnesium sulfate
  6. filtrationspontaneously filtered
  7. customthe filtrate obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe residue was recrystallized from isopropyl ether/n-hexane
  10. customdried (under reduced pressure at 40° C.)

Sources & evidence

ORD record
ord-5628e6afea2d47b58a42dcf74717235c
Source dataset
uspto-grants-2009_06
Patent number
US07541498B2

Reaction notes

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