Iodine → 1-Bromo-4-iodonaphthalene

Temperatur

-70 °C

100 g (350 mmol) of 1,4-dibromonaphthalene are initially introduced in 11 of THF, cooled to −70° C., and 235 ml of n-BuLi (1.6 M in hexane, 370 mmol) are added dropwise. After 1 h, 103 g (406 mmol) of I2 in 250 ml of THF are added dropwise, the mixture is stirred at −70° C. for a further 2 h, warmed to 0° C. and quenched by the addition of 50 ml (644 mmol) of aqueous NaHSO3 solution (w=39%). The phases are separated, and the aqueous phase is extracted once with MTB. The combined organic phases are washed with saturated sodium chloride soln., dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol, giving 1-iodo-4-bromonaphthalene as a yellow solid.

1. temperaturewarmed to 0° C.
2. customThe phases are separated
3. extractionthe aqueous phase is extracted once with MTB
4. washThe combined organic phases are washed with saturated sodium chloride soln
5. dry with material, dried over sodium sulfate
6. filtrationfiltered
7. customevaporated in a rotary evaporator
8. customThe residue is purified by column chromatography (SiO2, heptane)
9. customthe further purification
10. customis carried out by recrystallisation from isopropanol

ORD-Eintrag

ord-f0fbc23357924075aa3d1252886ca745

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09296948B2