Methyl 2-(4-fluorophenyl)acetate → HCID 18409455, Verbindung

HRID 993318

Reaktionsgleichung

Reaktionsgleichung von HRID 993318
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:23][S:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:31]([C:30]2[CH:29]=[CH:28][C:27]([S:24]([CH3:23])(=[O:26])=[O:25])=[CH:35][CH:34]=2)=[O:32])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 2733233Methyl 2-(4-fluorophenyl)acetateHCID 2733832Lithium HexamethyldisilazideHCID 112760134-(Methanesulfonyl)benzoyl chloride

Produkt 1

HCID 18409455HCID 18409455, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 mL), at −78° C., was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 mL, 14 mmol). After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 60 minutes at −78° C. and at 0 to 5° C. for 12 hours. The mixture was quenched with 10% citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69%). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J=9 Hz, 2H), 8.25 (d, J=9 Hz, 2H).

Aufarbeitung

  1. additionwas added in portions
  2. customThe mixture was quenched with 10% citric acid
  3. customthe THF removed in vacuo
  4. customthe residue triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-600ad2189e914b718105f1619e1337e8
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472416B1

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