Trichloro(chloromethyl)silane → Silane, dichloro(chloromethyl)phenyl-

HRID 1980529Notes

Reaction equation

HRID 1980529 reaction equation
[Cl:1][CH2:2][Si:3]([Cl:6])(Cl)[Cl:4].[C:7]1([Li])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[Cl:1][CH2:2][Si:3]([Cl:6])([Cl:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 15258Trichloro(chloromethyl)silaneHCID 178506676HCID 178506676, compound

Product 1

HCID 12747007Silane, dichloro(chloromethyl)phenyl-Yield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25.1 ml (36.8 g, 0.200 mol) of chloromethyltrichlorosilane in 400 ml dry tetrahydrofuran was cooled to -78° under nitrogen and stirred vigorously while 48.0 ml (0.100 mol) of 2.1 molar phenyllithium was slowly dripped in over 1 hour. After stirring another 30 minutes at -78° the solution was allowed to warm to room temperature and evaporated to about 200 ml. Addition of 500 ml ether, filtration to remove precipitated lithium chloride, and evaporation of the filtrate left 25.0 g of liquid. Distillation gave 6.5 g (29%) of the title compound as a colorless liquid: bp 62°-82° (0.15 mm); nmr (CDCl3): δ3.3 (s, 2) and 7.1-7.9 (m, 5).

Workup

  1. customwas slowly dripped in over 1 hour
  2. customevaporated to about 200 ml
  3. additionAddition of 500 ml ether, filtration
  4. customto remove
  5. customprecipitated
  6. customlithium chloride, and evaporation of the filtrate
  7. waitleft 25.0 g of liquid
  8. distillationDistillation

Sources & evidence

ORD record
ord-c3753a67601a481f8f676519bccbe353
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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