Hydrochloric Acid → Chloromethyldimethyl-2-phenylethylsilane

HRID 260636Notes

Reaction equation

HRID 260636 reaction equation
[C:1]1([CH2:7][CH2:8][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(CCBr)C=CC=CC=1.[Mg].Cl[Si:22]([CH2:25][Cl:26])([CH3:24])[CH3:23].Cl>O1CCCC1.O>[Cl:26][CH2:25][Si:22]([CH3:24])([CH3:23])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromideHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 5462224MagnesiumHCID 178419670HCID 178419670, compound

Product 1

HCID 22399658Chloromethyldimethyl-2-phenylethylsilaneYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-phenylethylmagnesium bromide, prepared from 2-phenylethyl bromide (9.25 g, 50 mmol) and magnesium (1.34 g, 55 mmol) in tetrahydrofuran (50 ml), is added chlorochlormethyldimethylsilane (6.43 g, 45 mmol) in tetrahydrofuran (25 ml). The mixture is refluxed for 18 hours, cooled to 0° C. and hydrolyzed with 3N HCl (50 ml). The mixture is then poured in water (50 ml) and diethyl ether (50 ml), the organic layer is washed with water, brine, dried over MgSO4 and the solvents removed in vacuo. Fractional distillation affords the title compound (5.15 g, 48.5% yield).

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. washdiethyl ether (50 ml), the organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. customthe solvents removed in vacuo
  5. distillationFractional distillation

Sources & evidence

ORD record
ord-6a12f37e08094ca1adf45eec0b590c59
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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