Carbon tetrabromide → (S)-2-(bromomethyl)-1-(cyclopentyl(methoxy)methyl)-4-(trifluoro-methyl)benzene

HRID 2075035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075035
[CH:1]1([CH:6]([O:19][CH3:20])[C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[CH2:17]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:22][CH2:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C@H:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[O:19][CH3:20]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58968669(2-(Cyclopentyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 58968705(S)-2-(bromomethyl)-1-(cyclopentyl(methoxy)methyl)-4-(trifluoro-methyl)benzeneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2-(cyclopentyl(methoxy)methyl)-5-(trifluoromethyl)phenyl)methanol (enatiomer 2 from the chiral separation of the racemate in STEP C, 23.1 mg, 0.080 mmol) and carbon tetrabromide (34.5 mg, 0.10 mmol) in methylene chloride (0.5 mL) at room temperature was added triphenyl phosphine (27.3 mg, 0.10 mmol). The mixture was stirred at room temperature overnight. Solvent was removed and the residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20-30% ethyl acetate in heptane) to afford the title compound (23.1 mg, 82%). 1H NMR (400 MHz, CDCl3) δ ppm 1.15-1.27 (m, 1H) 1.34-1.44 (m, 1H) 1.44-1.72 (m, 5H) 1.78-1.87 (m, 1H) 2.16-2.26 (m, 1H) 3.21 (s, 3H) 4.32 (d, J=7.88 Hz, 1H) 4.57 (d, J=10.37 Hz, 1H) 4.67 (d, J=10.37 Hz, 1H) 7.49-7.59 (m, 2H) 7.61 (s, 1H). The other enantiomer of the title compound was prepared in the same manner using enantiomer 1 from the chiral separation of the racemate in STEP C.

Aufarbeitung

  1. customSolvent was removed
  2. customthe residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20-30% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8c9ad066981d4f31b0173c3cc0d430d3
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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