Ethylene Glycol → 2-[(6-Bromo-2-naphthyl)thio]benzonitrile

HRID 735309ノート

反応式

HRID 735309 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([SH:12])[CH:6]=[CH:5]2.I[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].C(O)CO>[Cu]I.O.C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])[CH:6]=[CH:5]2

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 27593582-IodobenzonitrileHCID 197648176-Bromonaphthalene-2-thiol

生成物 1

HCID 689008402-[(6-Bromo-2-naphthyl)thio]benzonitrile

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

A mixture of 6-bromo-2-naphthyl hydrosulfide (Step 2, 2.08 g, 8.7 mmol), 2-iodobenzonitrile (2 g, 8.56 mmol), copper(I) iodide (83 mg, 0.44 mmol) and potassium carbonate (2.4 g, 17.4 mmol) was degassed then isopropyl alcohol (10 mL) and ethylene glycol (0.97 mL, 17.4 mmol) added. The reaction was heated to 80° overnight. The cooled reaction mixture was poured into water and extracted with dichloromethane (x3). The combined organic layers were washed with ammonium chloride solution, water and brine, filtered, dried over MgSO4 and evaporated in vacuo to give 2-[(6-bromo-2-naphthyl)thio]benzonitrile (2.85 g, containing some 2,2′-dithiobis(6-bromonaphthalene)). 2.19 g of this was treated according to the method of Example 2 Step 4 to give 2-[(6-bromo-2-naphthyl)sulfonyl]benzonitrile (1.33 g, 56%). 1H NMR (500 MHz, CDCl3) δ 8.76 (1H, s), 8.41 (1H, d, J=8.0 Hz), 8.07 (1H, s), 7.94-7.79 (5H, m), 7.72-7.68 (2H, m); m/z (ES+) 372, 374 [MH+].

後処理

  1. customwas degassed
  2. temperatureThe reaction was heated to 80° overnight
  3. customThe cooled reaction mixture
  4. extractionextracted with dichloromethane (x3)
  5. washThe combined organic layers were washed with ammonium chloride solution, water and brine
  6. filtrationfiltered
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-c5d2180029084903bd9de41f732af9a8
出典データセット
uspto-grants-2009_09
特許番号
US07592456B2

反応ノート

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