N-Fluorobenzenesulfonimide → [4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl](fluoro)acetonitrile

HRID 7721

Reaktionsgleichung

Reaktionsgleichung von HRID 7721
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[C:12]([Cl:19])[CH:11]=1.C([Li])(C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:35])(=O)=O)=CC=1>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([F:35])[C:17]#[N:18])=[C:12]([Cl:19])[CH:11]=1

Komponenten

5

Edukt 3

HCID 588007N-FluorobenzenesulfonimideHCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrileHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 21990957[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl](fluoro)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (98 mg, 0.36 mmol) and dry THF (5 mL) was cooled to −78° C. A solution of tert-butyllithium (500 μL, 0.80 mmol, 1.7M solution in pentane) was added dropwise via syringe at −78° C. After 1 h, a solution of N-fluorobenzenesulfonimide (113 mg, 0.36 mmol) and dry THF (1.5 mL) was added dropwise via syringe at −78° C. The cooling bath was removed, and the reaction mixture was gradually allowed to warm to rt, and was maintained at rt for 8 h. The reaction was quenched with silica gel (300 mg) and concentrated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc:hexanes, 1:3) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl](fluoro)acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.32 (s, 1H), 8.24 (2, 1H), 7.74–7.84 (m, 2H), 7.56–7.60 (m 1H), 7.35–7.43 (m, 2H), 6.45 (d, 1H). MS (ESI) 287 (M+H)+.

Aufarbeitung

  1. customThe cooling bath was removed
  2. temperaturewas maintained at rt for 8 h
  3. customThe reaction was quenched with silica gel (300 mg)
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash chromatography on silica gel (EtOAc:hexanes, 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-0a8906e3888144a3947ba02112964cb1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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