3-Methylbenzo[b]thiophene → 2-Fluoro-3-methyl-1-benzothiophene

HRID 10229

Reaktionsgleichung

Reaktionsgleichung von HRID 10229
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[B-](F)(F)(F)[F:12].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[F:12][C:3]1[S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1]

Komponenten

4

Edukt 2

HCID 738173-Methylbenzo[b]thiopheneHCID 2724933Selectfluor

Produkt 1

HCID 219783712-Fluoro-3-methyl-1-benzothiopheneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A stirred solution of 3-methylbenzothiophene (0.51 g, 3.37 mmol) in acetonitrile (5 μL) under nitrogen was treated with SELECTFLUOR™ (1.25 g, 3.35 mmol) and heated to 70° C. overnight. The solvent was removed in vacuo. The residue was taken up in ethyl acetate and washed with sodium hydrogen carbonate solution, water and brine, dried over MgSO4 and evaporated in vacuo. Purification by flash column chromatography on silica, eluting with isohexane, gave 2-fluoro-3-methyl-1-benzothiophene (72% pure, 190 mg, 0.82 mmol) which was treated according to the method of Example 29 Step 2 to give 3-(bromomethyl)-2-fluoro-1-benzothiophene (95 mg, 12%). 1H NMR (500 MHz, CDCl3) δ 7.75 (1H, d, J=8.0 Hz), 7.68 (1H, d, J=8.0 Hz), 7.46 (1H, t, J=7.6 Hz), 7.39–7.35 (1H, m), 4.65 (2H, s).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washwashed with sodium hydrogen carbonate solution, water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customPurification by flash column chromatography on silica
  6. washeluting with isohexane

Quellen und Nachweise

ORD-Eintrag
ord-25fc685f89c34fc6805c7197facceebe
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094777B2

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