Hydrochloric Acid → 2-Iodonaphthalene

HRID 1096733노트

반응식

HRID 1096733 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[I-:12].[K+].Cl>[Cu](I)I.CN(C)P(N(C)C)(N(C)C)=O>[I:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 113722-Bromonaphthalene

생성물 1

HCID 1364122-Iodonaphthalene수율 100%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
160 °C

실험 절차

2-Bromonapthalene (50.0 g, 242.0 mmol), copper iodide (230.0 g, 1210.0 mmol, 5 eq.), potassium iodide (200 g, 1210.0 mmol, 5 eq.) and hexamethylphosphoramide (500 mL) were stirred and heated to 160° C. for 8 h. This was cooled and added to 1N HCl (250 mL) then toluene (300 mL) and ether (300 mL) and the mixture filtered through celite. The organic layer was separated and washed with water (2×250 mL) dried over magnesium sulphate and concentrated to afford 2-iodonaphthalene (61.5 g, 59%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.46-7.52 (2H, m, ArH, 7.55-7.58 (1H, m, ArH), 7.68-7.74 (2H, m, ArH), 7.76-7.82 (1H, m, ArH), 8.22-8.26 (1H, m, ArH).

후처리

  1. temperatureThis was cooled
  2. filtrationtoluene (300 mL) and ether (300 mL) and the mixture filtered through celite
  3. customThe organic layer was separated
  4. washwashed with water (2×250 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-535ab3a6094f4779853b3af878ec9dfa
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138377B2

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