Hydrochloric Acid → Chloromethyl-dimethyl(4-fluorobenzyl)silane

HRID 260637Notes

Reaction equation

HRID 260637 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][Mg]Cl)=[CH:4][CH:3]=1.FC1C=CC(CCl)=CC=1.[Mg].Cl[Si:22]([CH2:25][Cl:26])([CH3:24])[CH3:23].Cl>CCOCC.CCCCCC>[Cl:26][CH2:25][Si:22]([CH3:24])([CH3:23])[CH2:6][C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 96024-Fluorobenzyl chlorideHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 5462224MagnesiumHCID 178505759HCID 178505759, compound

Product 1

HCID 15338764Chloromethyl-dimethyl(4-fluorobenzyl)silaneYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

To the 4-fluorobenzylmagnesiumchloride, prepared from parafluorobenzylchloride (1.59 g, 11 mmol) and magnesium (0.25 g, 11 mmol) in ether (20 ml), was added dropwise, at 0° C., chloro-chloromethyl-dimethylsilane (1.43 g, 10 mmol )in ether (5 ml). Then the mixture was refluxed 6 hours, cooled to 0° C., hydrolyzed with 3N HCl (20 ml) and extracted with ether. The ether solution was washed with water, brine, dried and evaporated. Chromatography (silica gel, hexane) afforded chloromethyl-dimethyl-4-fluorobenzyl silane as an oil (2.01 g, 93% yield) 1H NMR, CDCl3, TMS) δ: 0.20 (s,6H), 2.27 (s,2H), 2.63 (s,2H), 6.90-7.13 (m,4H).

Workup

  1. additionwas added dropwise, at 0° C.
  2. temperatureThen the mixture was refluxed 6 hours
  3. extractionextracted with ether
  4. washThe ether solution was washed with water, brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-cfb2a202511b4207afea450bd1bf446c
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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