Reaktion #1480814

Reaktionsgleichung

6-bromohexanoyl chloride

aniline

→

6-Bromohexanoic acid phenylamide

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Waschenthe solids rinsed with EtOAc
3. 3
   SonstigeThe residue was partitioned between H2O (15 mL) and EtOAc (20 mL)
4. 4
   Sonstigethe layers separated
5. 5
   ExtraktionThe aqueous portion was extracted with EtOAc (3×10 mL)
6. 6
   Waschenwashed with HCl (1 N), brine
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   EinengenConcentration under reduced pressure
10. 10
    workup.WAITleft a brown oil which
11. 11
    EinengenConcentration under reduced pressure

Vorschrift

To a solution of 6-bromohexanoyl chloride (1.00 mL, 6.53 mmol) in THF (35 mL) at 0° C. was added dropwise a solution of aniline (0.60 mL, 6.53 mmol) and TEA (1.09 mL, 7.84 mmol) in THF (5 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 2 h. The mixture was filtered, the solids rinsed with EtOAc, and the filtrate reduced under vacuum. The residue was partitioned between H2O (15 mL) and EtOAc (20 mL) and the layers separated. The aqueous portion was extracted with EtOAc (3×10 mL) and the organic layers combined, washed with HCl (1 N), brine, dried over MgSO4, and filtered. Concentration under reduced pressure left a brown oil which was passed through a plug of silica gel (30% EtOAc/hexanes) under aspiration. Concentration under reduced pressure left 67 as a solid (1.55 g, 5.74 mmol, 88%). TLC Rf 0.36 (25% EtOAc/hexanes); 1H-NMR (400 MHz, DMSO-d6) δ 9.85 (s, 1H), 7.57 (d, 2H), 7.27 (t, 2H), 7.01 (t, 1H), 3.53 (t, 2H), 2.30 (t, 2H), 1.81 (t, 2H), 1.63 (m, 2H), 1.42 (m, 2H); MS (ESI+) calcd for C12H16BrNO 268+270, found 269+271 [M+H]+.

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