Iodine → HCID 178429638, compound

HRID 2361550Notes

Reaction equation

HRID 2361550 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:17]=[C:16]([CH3:18])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH3:19])[CH:10]=1.[P:20]([O-:27])(OCC)OCC>O1CCCC1.C1(C)C=CC=CC=1.O>[CH3:14][N:13]([CH3:15])[C:12]1[C:11]([CH3:19])=[CH:10][C:9]([PH:20](=[O:27])[C:9]2[CH:17]=[C:16]([CH3:18])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH3:19])[CH:10]=2)=[CH:17][C:5]=1[CH3:6]

Participants

9

Reactant 5

HCID 807IodineHCID 78391,2-DibromoethaneHCID 1427314-bromo-N,N,2,6-tetramethylanilineHCID 3780918DiethylphosphiteHCID 5462224Magnesium

Product 1

HCID 178429638HCID 178429638, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, a solution of magnesium (2.4 g, 0.75 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in tetrahydrofuran (15 mL) was stirred at room temperature for 1 hr. A solution of 4-bromo-N,N,2,6-tetramethylaniline (31.2 g, 0.137 moL) synthesized in Reference Example 2 in tetrahydrofuran (50 mL) was added to the mixture at 25° C. to 30° C. over 1 hr, and the mixture was stirred at 40° C. for 1 hr. Then, a solution of diethyl phosphite (4.69 g, 0.25 equivalent) in tetrahydrofuran (15 mL) was added at 25° C. to 30° C. over 1 hr. Water (60 mL) was added to the mixture at 0° C. to 5° C., and then toluene (100 mL) was added to the mixture, and the insoluble material was removed by filtration. The filtrate was partitioned, and the organic layer was washed with water (30 mL) and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate) to give the title compound (4.6 g, colorless liquid). yield 40%.

Workup

  1. additionwas added to the mixture at 25° C. to 30° C. over 1 hr
  2. customthe insoluble material was removed by filtration
  3. customThe filtrate was partitioned
  4. washthe organic layer was washed with water (30 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6f38aa7609ea47a29a00dac7822c410f
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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