Tetrahydrofuran → Chloromethyl(4-fluorophenyl)divinylsilane

HRID 371308

Reaction equation

HRID 371308 reaction equation
[Cl:1][CH2:2][Si:3](Cl)(Cl)Cl.[F:7][C:8]1[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=1.[CH:16]([Mg]Br)=[CH2:17].O1CC[CH2:22][CH2:21]1>>[Cl:1][CH2:2][Si:3]([C:11]1[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=1)([CH:16]=[CH2:17])[CH:21]=[CH2:22]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 15258Trichloro(chloromethyl)silaneHCID 178418507HCID 178418507, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 13489942Chloromethyl(4-fluorophenyl)divinylsilane

Conditions

Temperature
0 °C

Procedure

To a solution of 6.3 ml (0.050 mol) of chloromethyltrichlorosilane in 75 ml of tetrahydrofuran cooled to -15° C. was added 25 ml of a 2.0 molar solution of p-fluorophenylmagnesium bromide (0.050 mol) at a rate that held the temperature below 0° C. The resulting suspension was stirred 30 minutes at 0° C. then allowed to warm to room temperature over 1 hour. A solution of vinylmagnesium bromide (71 ml, 1.4 molar in tetrahydrofuran) was then added, keeping the temperature below 35° C. The mixture was stirred 2 hours, then washed with saturated ammonium chloride. The aqueous layer was washed with ether-hexanes, and the combined organic layers were washed with brine, dried over sodium sulfate and evaporated. Kugelrohr distillation gave 7.25 g of the title compound as a colorless oil: nmr (CDCl3) 3.1 (2H, s), 5.8-6.7 (6H, m), 7.1, 7.7 (4H, two approximate t); ir (neat) 3060, 2955, 1590, 1497, 1402, 1232, 1162, 1105, 1006, 960, 821, 768 cm-1.

Workup

  1. customthe temperature below 0° C
  2. temperatureto warm to room temperature over 1 hour
  3. customthe temperature below 35° C
  4. stirringThe mixture was stirred 2 hours
  5. washwashed with saturated ammonium chloride
  6. washThe aqueous layer was washed with ether-hexanes
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-dfd3cdc8d99a4c178ad2c64f9569297b
Source dataset
uspto-grants-1985_07
Patent number
US04530922

Linked notes

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