Sodium Iodide → HCID 14279572, compound

HRID 622748Notes

Reaction equation

HRID 622748 reaction equation
[Br:1][C:2]([Br:30])=[CH:3][C:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)([CH3:21])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]=1.[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[Br:30][C:2]([Br:1])=[CH:3][C:4]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)([CH3:21])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14279571HCID 14279571, compound

Product 1

HCID 14279572HCID 14279572, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen atmosphere, 2.0 g of 1,1-dibromo-3-(4-methoxyphenyl)-3-methyl-6-(6-phenoxypyridin-2-yl)-1-hexene were dissolved in 50 ml of dry acetonitrile, and 1.69 g of sodium iodide and 1.23 g of trimethylsilyl chloride were added thereto. The mixture was then heated under reflux for 6 hours. The reaction solution was poured into ice water and extracted twice with ethyl acetate. The ethyl acetate layer was successively washed with an aqueous dilute sodium sulfite solution and a saturated aqueous sodium chloride solution. The solvent was then removed by evaporation under reduced pressure to obtain 1.81 g of the desired 1,1-dibromo-3-(4-hydroxyphenyl)-3-methyl-6-(6-phenoxypyridin-2-yl)-1-hexene.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted twice with ethyl acetate
  4. washThe ethyl acetate layer was successively washed with an aqueous dilute sodium sulfite solution
  5. customThe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d09bc50a2c354d18aff26f7e545039a0
Source dataset
uspto-grants-1988_09
Patent number
US04772633

Reaction notes

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