Hydrofluoric Acid → Chloromethyl(fluoro)[bis(4-fluorophenyl)]silane

HRID 1980528Notes

Reaction equation

HRID 1980528 reaction equation
[Cl:1][CH2:2][Si:3]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)OC(C)C.[FH:22]>C(O)C>[Cl:1][CH2:2][Si:3]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 13392402Chloromethyl[bis(4-fluorophenyl)](2-propoxy)silane

Product 1

HCID 20401763Chloromethyl(fluoro)[bis(4-fluorophenyl)]silaneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.0 g (33.7 mmol) of chloromethyl[bis(4-fluorophenyl)](2-propoxy)silane and 10 ml of 49% aqueous hydrofluoric acid in ethanol was refluxed for 2 hours under nitrogen, cooled, and partitioned between water and ether. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated to leave 9.7 g (100%) of chloromethyl(fluoro)[bis(4-fluorophenyl)]silane as a mobile oil: nD22 1.5387; nmr (CDCl3) 3.2 (2H, d), 7.2 (4H, t), 7.8 (4H, d of d).

Workup

  1. temperaturecooled
  2. custompartitioned between water and ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ed163721dc1e4a25a42ea8dab2953d25
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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