HCID 13392413, compound → HCID 13489945, compound

HRID 371311Notes

Reaction equation

HRID 371311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH:10]([Cl:12])[CH3:11])Cl)=[CH:4][CH:3]=1.F[C:21]1[CH:26]=CC([Si](C2C=CC(F)=CC=2)(CCCl)Cl)=C[CH:22]=1.C([Mg]Br)C=C>O1CCCC1.[Cl-].[NH4+].O>[CH2:26]([Si:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:10]([Cl:12])[CH3:11])[CH:21]=[CH2:22]

Participants

7

Reactant 3

HCID 13392413HCID 13392413, compoundHCID 13392414HCID 13392414, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 13489945HCID 13489945, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 20 g (63 mmol) of a 1:1 mixture of bis(4-fluorophenyl)-1-chloroethyl(chloro)silane and bis(4-fluorophenyl)-2-chloroethyl(chloro)silane in 100 ml of tetrahydrofuran is treated dropwise with 71 ml (71 mmol) of 1.0 molar allyl magnesium bromide in tetrahydrofuran. The mixture is refluxed two hours, cooled, and diluted with saturated aqueous ammonium chloride and water. The aqueous phase is separated and extracted with ether, and the combined organic phases are washed with water and brine, dried over sodium sulfate, and evaporated to give the title compounds as a 1:1 mixture.

Workup

  1. temperatureThe mixture is refluxed two hours
  2. temperaturecooled
  3. customThe aqueous phase is separated
  4. extractionextracted with ether
  5. washthe combined organic phases are washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6ecbc4b20bcb46cc9cec20319797f1ec
Source dataset
uspto-grants-1985_07
Patent number
US04530922

Reaction notes

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