1,3-Dibromopropane → 1-(3-Bromopropoxy)-2-fluorobenzene

HRID 533843

Reaktionsgleichung

Reaktionsgleichung von HRID 533843
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9][CH2:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:12][CH2:11][CH2:10][Br:9]

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 97072-FluorophenolHCID 10796Cesium carbonate

Produkt 1

HCID 71722931-(3-Bromopropoxy)-2-fluorobenzeneAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-fluorophenol (0.040 mL, 0.448 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.450 mL, 4.43 mmol) followed by Cs2CO3 (0.232 g, 0.713 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (8 mL). The organic layer was dried through a phase separator and concentrated under vacuum. The residue was taken up in DMSO and purified by preparatory HPLC (without TFA) to give the title compound (0.0274 g, 26.2%). EI-MS Rt (2.24 min).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionThe resulting residue was treated with H2O (4 mL)
  3. extractionextracted with DCM (8 mL)
  4. customThe organic layer was dried through a phase separator
  5. concentrationconcentrated under vacuum
  6. custompurified by preparatory HPLC (without TFA)

Quellen und Nachweise

ORD-Eintrag
ord-75daea08891645c2b76ac5cb1a1e57d2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853404B2

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