Reaktion #91368

ord-db2e70e06ffa4211ab8ab64968b3a57e

Reaktionsgleichung

COc1ccc2c(c1)CCCC2=O
6-methoxy-1-tetralone
F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
Selectfluor
COc1ccc2c(c1F)CCCC2=O
title compound
Ausbeute 42.1%
COc1ccc2c(c1F)CCCC2=O
5-fluoro-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one
Ausbeute 42.1%

Lösungsmittel

Reaktionsbedingungen

Temperatur
40°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction was filtered
  2. 2
    Einengenconcentrated
  3. 3
    workup.DISSOLUTIONThe residue was dissolved in EtOAc (40 mL)
  4. 4
    Filtrationfiltered
  5. 5
    Einengenconcentrated
  6. 6
    SonstigePurification by silica gel chromatography (PE/EtOAc/DCM=20:1:2)

Vorschrift

To a solution of 6-methoxy-1-tetralone (200 mg, 1.1 mmol) in ACN (20 mL) was added Selectfluor (603 mg, 1.7 mmol) at rt, and the reaction was stirred at 40° C. overnight. The reaction was filtered and concentrated. The residue was dissolved in EtOAc (40 mL), filtered, and concentrated. Purification by silica gel chromatography (PE/EtOAc/DCM=20:1:2) gave 90 mg (41%) of the title compound as a yellow solid. [M+H] Calc'd for C11H11FO2, 195. Found, 195.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447045B2uspto-grants-2016_09