Boron tribromide → 6-Chloro-2'-fluoro-4-iodobiphenyl-3-ol

HRID 1619695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619695
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[C:10]([I:12])[C:9]([O:13]C)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]>ClCCl>[Cl:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[CH:8][C:9]([OH:13])=[C:10]([I:12])[CH:11]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

Produkt 1

HCID 580423466-Chloro-2'-fluoro-4-iodobiphenyl-3-olAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Boron tribromide (251 mg, 2.61 mmol) was added to a solution of 2-chloro-2′-fluoro-4-iodo-5-methoxybiphenyl (Preparation 95, 671 mg, 1.85 mmol) in dichloromethane (4.7 mL) at −20° C. and the mixture allowed to warm slowly to room temperature for 18 hours. The reaction was quenched by addition of water (10.0 mL), before being diluted with dichloromethane (30 mL). The organic phase was separated and washed with water (3×5.0 mL), brine (5.0 mL), dried over MgSO4, filtered and evaporated to give a purple oil. Column chromatography purification on silica, eluting with 1:4 ethyl acetate:heptanes gave the title compound (610 mg, 94%) as a colourless oil.

Aufarbeitung

  1. customThe reaction was quenched by addition of water (10.0 mL)
  2. additionbefore being diluted with dichloromethane (30 mL)
  3. customThe organic phase was separated
  4. washwashed with water (3×5.0 mL), brine (5.0 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a purple oil
  9. customColumn chromatography purification on silica
  10. washeluting with 1:4 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7566a60786ce43b98753b3a12d84156d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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