Iodine → HCID 19781372, compound

HRID 1252740Notes

Reaction equation

HRID 1252740 reaction equation
[Mg].[CH3:2][Si:3](Cl)([Cl:5])[Cl:4].II.BrC(Br)C.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>C(OCC)C>[CH3:2][Si:3]([Cl:5])([Cl:4])[CH2:19][C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 807IodineHCID 6399TrichloromethylsilaneHCID 112011,1-DibromoethaneHCID 699934-Methyloxybenzyl chlorideHCID 5462224Magnesium2×

Product 1

HCID 19781372HCID 19781372, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 1-liter three-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer were placed 23.3 g (1.00 mol) of magnesium powder, 82.6 g (0.640 mol) of methyltrichlorosilane, and 200 ml of diethyl ether. The magnesium was activated with iodine and dibromoethane. The flask was cooled to 10° C. to 0° C. A mixture of 50.0 g (0.319 mol) of p-methoxybenzyl chloride and 300 ml of diethyl ether was added dropwise with stirring from the dropping funnel over 4 hours at 10° C. to 0° C. After aging at room temperature for 1 hour, excess magnesium and magnesium chloride were removed by suction filtration. The filtrate was distilled to give 48.8 g (0.208 mol) of the desired product in a yield of 65%.

Workup

  1. customIn a 1-liter three-neck flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureThe flask was cooled to 10° C. to 0° C
  4. additionwas added dropwise
  5. waitAfter aging at room temperature for 1 hour
  6. customexcess magnesium and magnesium chloride were removed by suction filtration
  7. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-e38309a9548c4562af6c2a074a9770cb
Source dataset
uspto-grants-1988_05
Patent number
US04745169

Reaction notes

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