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

HRID 735309노트

반응식

HRID 735309 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-c5d2180029084903bd9de41f732af9a8
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592456B2

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