Phosphorus tribromide → 2-(Bromomethyl)-6-fluoronaphthalene

HRID 333229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333229
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12]O)[CH:6]=[CH:5]2.P(Br)(Br)[Br:15]>C(Cl)Cl>[Br:15][CH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 58954787(6-Fluoronaphthalen-2-yl)methanol

Produkt 1

HCID 5946332-(Bromomethyl)-6-fluoronaphthaleneAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (6-fluoro-naphthalen-2-yl)-methanol (2.0 g, 11.3 mmol) in CH2Cl2 (30 mL) was added PBr3 (1.0 M in CH2Cl2, 22.6 mmol). The reaction mixture was stirred for 3 h at room temperature before being quenched by NH4Cl (30 mL). The organic layer was separated, dried and concentrated. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:10) to afford 2-bromomethyl-6-fluoro-naphthalene (2.23 g, 74%).

Aufarbeitung

  1. custombefore being quenched by NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-d8abc23c2dda45158b33302e8b32cff6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877975B2

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