Iodine → HCID 178436979, compound

HRID 875282Notes

Reaction equation

HRID 875282 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:17]=[C:16]([CH2:18][CH3:19])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH2:20][CH3:21])[CH:10]=1.[P:22]([O-:29])(OCC)OCC>O1CCCC1.C(OCC)(=O)C.O>[CH3:14][N:13]([CH3:15])[C:12]1[C:11]([CH2:20][CH3:21])=[CH:10][C:9]([PH:22](=[O:29])[C:9]2[CH:17]=[C:16]([CH2:18][CH3:19])[C:12]([N:13]([CH3:15])[CH3:14])=[C:11]([CH2:20][CH3:21])[CH:10]=2)=[CH:17][C:16]=1[CH2:5][CH3:6]

Participants

9

Reactant 5

HCID 807IodineHCID 78391,2-DibromoethaneHCID 3780918DiethylphosphiteHCID 5462224MagnesiumHCID 14146117HCID 14146117, compound

Product 1

HCID 178436979HCID 178436979, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Under an argon atmosphere, a solution of magnesium (2.8 g, 1.0 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in tetrahydrofuran (15 mL) was stirred at room temperature for 30 min. A solution of 4-bromo-2,6-diethyl-N,N-dimethylaniline (29.4 g, 0.115 moL) synthesized in Reference Example 3 in tetrahydrofuran (50 mL) was added to the mixture at 20° C. to 25° C. over 1 hr, and the mixture was stirred at 40° C. for 1 hr. Then, a solution of diethyl phosphite (4.01 g, 0.25 equivalent) in tetrahydrofuran (8 mL) was added at 20° C. to 25° C. over 1 hr. Water (90 mL) was added to the mixture at 5° C. to 10° C., and then ethyl acetate (100 mL) was added to the mixture. The mixture was partitioned, and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate) to give the title compound (8.34 g, colorless liquid). yield 72%.

Workup

  1. additionwas added to the mixture at 20° C. to 25° C. over 1 hr
  2. customThe mixture was partitioned
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 100 g, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3ffd34e87a434730afb05267a6e678cb
Source dataset
uspto-grants-2015_03
Patent number
US08981147B2

Reaction notes

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