4-Bromo-2,6-xylidine → N-(4-Bromo-2,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl) dimethylsilanamine

Under an argon atmosphere, to a solution of 12.4 g (61.9 mmol) of 4-bromo-2,6-dimethylaniline in 300 ml of THF, 16.5 ml of 2.5 M (41.2 mmol) nBuLi in hexanes was added at −80° C. This mixture was warmed for ca. 2 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 10.0 g (41.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 50 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 154-156° C./0.05 mm Hg. The product crystallizes slowly at ambient temperature. Yield 8.36 g (50%).

1. temperatureThis mixture was warmed for ca. 2 hour to ambient temperature
2. additionThen, the resulting solution was added dropwise over ca. 1 hour
3. customevaporated to dryness
4. additionTo the residue, 150 ml of toluene was added
5. filtrationThis mixture was filtered through a glass frit (G4)
6. customThe filtrate was evaporated to dryness
7. distillationFractional distillation
8. customgave a yellow liquid, bp 154-156° C./0.05 mm Hg
9. customThe product crystallizes slowly at ambient temperature

ORDレコード

ord-132c5cccf0824010b49ca1517a54cacb

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07868197B2