Carbon tetrabromide → 2'-(Bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

HRID 1994599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994599
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[F:25][C:26]1[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:29]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2CO)=[C:28]([O:47][CH3:48])[C:27]=1[OH:49]>C(Cl)Cl>[Br:24][CH2:20][C:36]1[CH:37]=[C:38]([C:41]([F:44])([F:42])[F:43])[CH:39]=[CH:40][C:35]=1[C:29]1[CH:30]=[C:31]([CH:32]([CH3:34])[CH3:33])[C:26]([F:25])=[C:27]([OH:49])[C:28]=1[O:47][CH3:48]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 866034354-Fluoro-2'-(hydroxymethyl)-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

Produkt 1

HCID 866034362'-(Bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4'-(trifluoromethyl)biphenyl-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (102.8 mg, 0.392 mmol) in dry CH2Cl2 (2 mL) was added by cannula to a stirred solution of carbon tetrabromide (130 mg, 0.392 mmol) and 4-fluoro-2′-(hydroxymethyl)-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl-3-ol (58.5 mg, 0.163 mmol) in dry CH2Cl2 (2 mL) at 0° C. under N2 and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-40% EtOAc in hexanes gradient) to afford 2′-(bromomethyl)-4-fluoro-5-isopropyl-2-methoxy-4′-(trifluoromethyl)biphenyl-3-ol. Rf=0.55 (20% EtOAc in hexanes). 1H NMR (600 MHz, CDCl3) δ 7.84 (s, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 6.69 (d, J=7.8 Hz, 1H), 5.59 (s, 1H), 4.50 (d, J=9.6 Hz, 1H), 4.39 (d, J=9.7 Hz, 1H), 3.47 (s, 3H), 3.29-3.23 (m, 1H), 1.27 (d, J=6.9 Hz, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Si, 12×160 mm, 0-40% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6bd3810878904f99aa177d14a1d0f394
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652049B2

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