Iodine → Silane, (4-chlorophenyl)dimethyl-

Temperature

50 °C

About 9 kg of 1,4-dichlorobenzene (60 mol) were dissolved in 10.2 liters of tetrahydrofuran. About 1,440 g of magnesium turnings activated with iodine were introduced into a 50 liter stirred kettle. About 1.4 liters of tetrahydrofuran and 600 ml of 1,4-dichlorobenzene solution were then added, and the mixture was warmed to 50° C. The reaction was initiated by adding a few ml of ethyl bromide. The dichlorobenzene solution was added over a period of about 4 hours, the reaction temperature being kept between 60° and 63° C. When all the dichlorobenzene had been added, the reaction mixture was allowed to stand for 2.5 hours at 60° C. to complete the reaction. The reaction mixture was then cooled, diluted with 6 liters of tetrahydrofuran and transferred into a dropping funnel. The conversion was determined by weighing the unreacted magnesium. It was 88 percent by weight. Accordingly, 52.9 mol of dimethylchlorosilane in 12 liters of methyl tert-butyl ether were introduced into the 50 liter stirred kettle. The Grignard solution was added through the dropping funnel at a rate such that it was possible to keep the temperature at 30° C. with cooling. The reaction mixture was then stirred for an additional 30 minutes at room temperature. Sufficient water was added to the crystal slurry so that two homogeneous phases formed. The organic phase was separated off, and the aqueous phase was extracted once with methyl tert-butyl ether. The crude product was distilled in a water-pump vacuum. About 6,305 g of (4-chlorophenyl)dimethylsilane were obtained, which amounted to a yield of about 70 percent by weight, based on the amount of dichlorobenzene reacted.

1. additionwere introduced into a 50 liter
2. custombeing kept between 60° and 63° C
3. customthe reaction
4. temperatureThe reaction mixture was then cooled
5. customtransferred into a dropping funnel
6. stirringstirred kettle
7. additionThe Grignard solution was added through the dropping funnel at a rate such that it
8. customat 30° C.
9. temperaturewith cooling
10. stirringThe reaction mixture was then stirred for an additional 30 minutes at room temperature
11. customformed
12. customThe organic phase was separated off
13. extractionthe aqueous phase was extracted once with methyl tert-butyl ether
14. distillationThe crude product was distilled in a water-pump vacuum

ORD record

ord-47a97d1988444b8481ab19236ceb6cd9

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04914221