Water → (1,3-Benzodioxol-5-yl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane

HRID 1639239Notes

Reaction equation

HRID 1639239 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])Cl)=[CH:19][C:18]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O>C(OCC)C>[O:6]1[C:5]2[CH:9]=[CH:10][C:2]([Si:26]([CH2:25][CH2:24][CH2:23][C:20]3[CH:21]=[CH:22][C:17]([F:16])=[C:18]([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:19]=3)([CH3:29])[CH3:28])=[CH:3][C:4]=2[O:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 19838762[3-(4-Fluoro-3-phenoxyphenyl)propyl]dimethylchlorosilaneHCID 178418339Butyllithium

Product 1

HCID 14601814(1,3-Benzodioxol-5-yl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilaneYield 40.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.21 g (0.0060 mole) of 5-bromo-1,3-benzodioxole in 30 mL of dry diethyl ether that had been cooled to -78° C. was added during a 15 minute period 0.42 g (0.0065 mole) of butyllithium as a 2.5 M solution in hexanes. Upon completion of addition this mixture was stirred at -78° C. for one hour. During a 20 minute period 1.9 g (0.006 mole) of [3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylchlorosilane was added as the solution prepared in Part D. The reaction mixture was allowed to warm to room temperature and to stir for an additional hour. Water was added to the reaction mixture which was then extracted With diethyl ether. The ether extract was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated under reduced pressure, leavinq a residue weighing approximately 3 g. This residue was passed through a column of silica gel, eluting with methylene chloride/hexane (1/9). This procedure yielded 1.0 g of (1,3-benzodioxol-5-yl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane as a clear, colorless liquid, compound 43 of Table 1. The ir spectrum and the proton, carbon, and fluorine nmr spectra were all consistent with the proposed structure.

Workup

  1. additionUpon completion of addition this mixture
  2. customprepared in Part D
  3. temperatureto warm to room temperature
  4. stirringto stir for an additional hour
  5. extractionwas then extracted With diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure
  10. washeluting with methylene chloride/hexane (1/9)

Sources & evidence

ORD record
ord-067ca144434a447e95bcbe43f67dae0b
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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