Ethyl Acetate → 4-[(4-Fluorophenyl)sulfanyl]aniline

HRID 510150노트

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HRID 510150 반응식
[Cl-].[NH4+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.C(OCC)(=O)C>O.CO.O1CCCC1.[Fe]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

참가 물질

8

반응물 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 27830591-Fluoro-4-[(4-nitrophenyl)sulfanyl]benzene

생성물 1

HCID 27747404-[(4-Fluorophenyl)sulfanyl]aniline수율 85%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

To a solution of ammonium chloride (16.63 g, 311 mmol) in water (300 mL) are added iron (17.39 g, 311 mmol) and a solution of 1-fluoro-4-(4-nitrophenyl)sulfanyl-benzene (19.40 g, 78 mmol) in a mixture of methanol (100 mL) and tetrahydrofuran (100 mL). The resulting mixture is heated to 75° C. for 2.5 h and then cooled to room temperature. After addition of ethyl acetate (1 L), the mixture is stirred for 10 min the organic layer is decanted and collected. This procedure is repeated twice. The combined organic layers are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude residue is first triturated twice with diethyl ether and then purified via column chromatography on silica gel (heptane/ethyl acetate 0 to 30% as eluent) to afford the desired product as a yellow solid (14.45 g, 66 mmol, 85% yield) (HPLC-MS Method 2: retention time: 1.939 min, m/z 261.0).

후처리

  1. temperaturecooled to room temperature
  2. customis decanted
  3. customcollected
  4. dry with materialThe combined organic layers are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue is first triturated twice with diethyl ether
  8. custompurified via column chromatography on silica gel (heptane/ethyl acetate 0 to 30% as eluent)

출처 및 근거

ORD 기록
ord-0d313d4c469b4913ad6bd87353d98241
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096599B2

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