Iodine → 4-Fluoro-2'-(iodomethyl)-5-isopropyl-4'-(trifluoromethyl)biphenyl-2-ol

HRID 1028623

Reaktionsgleichung

Reaktionsgleichung von HRID 1028623
[F:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[CH2:21]O)=[C:4]([O:23]C)[CH:3]=1.[I:25]I>C1([Si](C)(C)C)C=CC=CC=1.Cl>[F:1][C:2]1[CH:3]=[C:4]([OH:23])[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[CH2:21][I:25])=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Komponenten

5

Edukt 2

HCID 807IodineHCID 533638284'-Fluoro-2'-methoxy-5'-(1-methylethyl)-4-(trifluoromethyl)(1,1'-biphenyl)-2-methanol

Produkt 1

HCID 667166694-Fluoro-2'-(iodomethyl)-5-isopropyl-4'-(trifluoromethyl)biphenyl-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 69849PhenyltrimethylsilaneLösungsmittel

Versuchsvorschrift

A solution of [4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol (71.5 mg, 0.209 mmol) and iodine (610 mg, 2.40 mmol) in phenyltrimethylsilane (877 μL) was heated at 110° C. in a sealed tube overnight. The reaction was cooled to room temperature, diluted with 1N HCl (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were washed with 10% Na2S2O3 (20 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient) to afford 4-fluoro-2′-(iodomethyl)-5-isopropyl-4′-(trifluoromethyl)biphenyl-2-ol. Rf=0.65 (20% EtOAc in hexanes). 1H NMR (500 MHz, CDCl3) δ 7.81 (s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.34 (d, J=7.9 Hz, 1H), 7.10 (d, J=8.3 Hz, 1H), 6.69 (d, J=11.1 Hz, 1H), 4.82 (s, 1H), 4.41 (d, J=9.4 Hz, 1H), 4.23 (d, J=9.3 Hz, 1H), 3.27-3.19 (m, 1H), 1.27 (br s, 6H).

Aufarbeitung

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined extracts were washed with 10% Na2S2O3 (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThis was purified by flash chromatography (Si, 12×160 mm, 0-20% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-86bc61dc609745dcb30f200b3907cc24
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735435B2

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