Hexane → 4-(2,2-Dibromovinyl)-4'-pentylbiphenyl

Temperature

0 °C

A solution of 15.3 g of tetrabromomethane in 150 ml of methylene chloride was placed at 0° C. in a sulphonation flask under argon gasification and treated within 5 minutes with a solution of 12.1 g of triphenylphosphine in 50 ml of methylene chloride. After completion of the addition, the clear orange reaction solution was stirred at 0° C. for a further 5 minutes and then a solution of 5.80 g of 4-formyl-4'-pentylbiphenyl in 50 ml of methylene chloride was added dropwise within 10 minutes. After stirring at 0° C. for a further 45 minutes, the yellow-orange mixture was poured into 1000 ml of hexane and the precipitate which thereby separated was filtered off (rinsing with hexane). The concentrated filtrate was digested with 400 ml of hexane, left to stand at 0° C. for 18 hours, filtered (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (9.8 g) on silica gel with hexane gave 5.15 g (55%) of 4-(2,2-dibromovinyl)-4'-pentylbiphenyl as colourless crystals (purity 99.1%); m.p. 95° C.

1. additionAfter completion of the addition
2. stirringAfter stirring at 0° C. for a further 45 minutes
3. customthe precipitate which thereby separated
4. filtrationwas filtered off
5. wash(rinsing with hexane)
6. waitleft
7. waitto stand at 0° C. for 18 hours
8. filtrationfiltered
9. wash(rinsing with hexane)
10. concentrationthe filtrate was concentrated

ORD record

ord-0f5f3bfb8f0f4b018277b9e2b4681e44

Source dataset

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04528114