Sulfuric Acid → 4-Amino-3-fluoro-5-iodobenzonitrile

HRID 400598

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HRID 400598 반응식
B(O[O-])=O.[Na+].[I-:6].[K+].S(=O)(=O)(O)O.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21]C(=O)C)=[C:17]([F:25])[CH:16]=1)#[N:14].S([O-])([O-])(=O)=S.[Na+].[Na+].S(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[NH2:21][C:18]1[C:19]([I:6])=[CH:20][C:15]([C:13]#[N:14])=[CH:16][C:17]=1[F:25]

참가 물질

11

반응물 6

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 517072Sodium PerborateHCID 11344323Acetamide, N-(4-cyano-2-fluorophenyl)-HCID 23665763Sodium Bisulfite

생성물 1

HCID 442031204-Amino-3-fluoro-5-iodobenzonitrile수율 15.3%

시약·촉매·용매 4

HCID 26052Sodium tungstate촉매HCID 176Acetic Acid용매2회HCID 962Water용매HCID 7918Acetic Anhydride용매

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온도
50 °C

실험 절차

A solution of sodium perborate (4.2 g, 27.3 mmols) and sodium tungstate (450 mg, 1.4 mmol) in a mixture of 20 mL of glacial acetic acid and 15 mL of acetic anhydride was treated with a solution of potassium iodide (2.3 g, 13.9 mmols) in 15 mL of water. The mixture was treated with 7.5 mL of concentrated sulfuric acid over 15 minutes. A suspension of N-(4-cyano-2-fluorophenyl)acetamide (1.79 g, 10 mmols) in 15 mL of glacial acetic acid was added to and the resulting mixture was heated at 50° C. After 1 hour, the mixture was poured into 300 mL of crushed ice and treated with 100 mL of a saturated solution of sodium thiosulfate followed by 100 mL of a sodium bisulfite solution. The mixture was extracted with three 100 mL portions of dichloromethane and the combined organic layers were washed with three 50 mL portions of sodium bicarbonate solution, three 50 mL portions of water, dried over sodium sulfate, and concentrated in vacuo to give a light brownish solid. Chromatography on SiO2 (50% ethyl acetate in hexanes) afforded 400 mg of the title product as a light brownish solid (15% yield).

후처리

  1. additionwas added to and the resulting mixture
  2. extractionThe mixture was extracted with three 100 mL portions of dichloromethane
  3. washthe combined organic layers were washed with three 50 mL portions of sodium bicarbonate solution, three 50 mL portions of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a light brownish solid

출처 및 근거

ORD 기록
ord-a46a63f8240a49a9b730c667efb6ac83
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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