Hydrochloric Acid → 2-Iodonaphthalene

HRID 1096733ノート

反応式

HRID 1096733 の反応式
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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 113722-Bromonaphthalene

生成物 1

HCID 1364122-Iodonaphthalene収率 100%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-535ab3a6094f4779853b3af878ec9dfa
出典データセット
uspto-grants-2012_03
特許番号
US08138377B2

反応ノート

読み込み中…