Iodine → 1-Bromo-4-iodonaphthalene

HRID 403065

반응식

HRID 403065 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Br)=[CH:4][CH:3]=1.[Li]CCCC.[I:18]I.OS([O-])=O.[Na+]>C1COCC1>[I:18][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][CH:4]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 665211,4-DibromonaphthaleneHCID 23665763Sodium BisulfiteHCID 178418339Butyllithium

생성물 1

HCID 50736671-Bromo-4-iodonaphthalene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

100 g (350 mmol) of 1,4-dibromonaphthalene are initially introduced in 1 l 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 of I2 (406 mmol) 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 solution, 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.

후처리

  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 solution
  5. dry with materialdried 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

출처 및 근거

ORD 기록
ord-3d0b8e4d202d4c0daf61019d5cc40b59
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08747695B2

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