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

HRID 510150ノート

反応式

HRID 510150 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0d313d4c469b4913ad6bd87353d98241
出典データセット
uspto-grants-2015_08
特許番号
US09096599B2

反応ノート

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