Acetic Acid → 1-Chloro-2-fluoro-4-iodo-5-methoxybenzene

HRID 1473574ノート

反応式

HRID 1473574 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[F:10].CC(O)=O.S(=O)(=O)(O)O.C1C(=O)N([I:27])C(=O)C1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:27])=[CH:4][C:3]=1[F:10]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 27735853-Chloro-4-fluoroanisole

生成物 1

HCID 210706301-Chloro-2-fluoro-4-iodo-5-methoxybenzene収率 70.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A round-bottom flask was charged with 2-chloro-1-fluoro-4-methoxybenzene (Alfa Aesar, Ward Hill, Mass., 2.714 g, 16.90 mmol), DCM (24.86 ml), AcOH (24.86 ml), and sulfuric acid (0.496 ml, 9.30 mmol) to give a solution. n-iodosuccinimide (3.80 g, 16.90 mmol) was added in a single portion. TLC showed what appeared to be conversion of the starting material to a slightly higher, move UV-active spot. The mixture was diluted with DCM, washed with water (2×), washed with saturated aq. sodium thiosulfate, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-10% EtOAc/Heptane) to give 3.409 g of a clear oil. This oil was used directly in the next reaction without further purification.

後処理

  1. customto give a solution
  2. washwashed with water (2×)
  3. washwashed with saturated aq. sodium thiosulfate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 0-10% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-0323f11afe314e979ec1f231d4171d33
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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