Carbon tetrabromide → 2-Bromomethyl-4'-fluorobiphenyl

HRID 1877918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877918
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14]O)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:17][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1392777(4'-Fluorobiphenyl-2-yl)methanol

Produkt 1

HCID 114484672-Bromomethyl-4'-fluorobiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (4′-fluorobiphenyl-2-yl)-methanol (2.58 g, 12.8 mmol) in CH2Cl2 (100 mL), carbon tetrabromide (7.40 g, 22.3 mmol) is added. The solution is cooled to 0° C. and then triphenylphosphine (7.53 g, 28.7 mmol) is added portionwise. The reaction is stirred at 0° C. for 1.5 h and then at room temperature for 90 h before the solvent is removed. The resulting residue is partitioned between Et2O and water and then filtered. The layers are separated and the aqueous layer is extracted with Et2O. The combined organic layers are washed with water, brine and dried over Na2SO4. After concentration, the residue is purified by flash chromatography (hexane) to give 2-bromomethyl-4′-fluorobiphenyl as an oil. (an alternative preparation appears in J. Med. Chem. 2004, 47(22), 5441) 1H NMR (400 MHz, CDCl3) δ 7.53-7.50 (m, 1H), 7.43-7.31 (m, 4H), 7.24-7.21 (m, 1H), 7.15-6.80 (m, 2H), 4.42 (s, 2H).

Aufarbeitung

  1. customat room temperature for 90 h before the solvent is removed
  2. customThe resulting residue is partitioned between Et2O and water
  3. filtrationfiltered
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with Et2O
  6. washThe combined organic layers are washed with water, brine
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration
  9. customthe residue is purified by flash chromatography (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d44d4943d0774eb99de7072dff6c2230
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314097B2

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