N-Iodosuccinimide → 2-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

HRID 1619696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619696
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]>S(=O)(=O)(O)O.C(O)(=O)C.ClCCl>[Cl:9][C:10]1[CH:15]=[C:14]([I:1])[C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]

Komponenten

6

Edukt 2

HCID 120273N-IodosuccinimideHCID 580422982-Chloro-2'-fluoro-5-methoxybiphenyl

Produkt 1

HCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenylAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-Iodosuccinimide (683 mg, 3.04 mmol) was added to a solution of 2-chloro-2′-fluoro-5-methoxybiphenyl (Preparation 96, 749 mg, 3.16 mmol) in concentrated sulfuric acid (0.09 mL), acetic acid (4.7 mL) and dichloromethane (4.7 mL). The resulting mixture was stirred at room temperature for 18 hours and then partitioned between dichloromethane (30 mL) and water (5 mL). The organic phase was separated and washed with water (2×5 mL), brine (5 mL), dried over MgSO4, filtered and evaporated to give a red oil. Column chromatography purification on silica, eluting with dichloromethane:heptanes (1:9) gave the title compound (671 mg, 58%) as a colourless oil.

Aufarbeitung

  1. custompartitioned between dichloromethane (30 mL) and water (5 mL)
  2. customThe organic phase was separated
  3. washwashed with water (2×5 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customColumn chromatography purification on silica
  9. washeluting with dichloromethane:heptanes (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-d62db1b14fc1499eb54ec3a4b2cc7148
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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