Nitric Acid → 2-Nitro-5-(trifluoromethoxy)benzyl bromide

HRID 505277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505277
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:17])([F:16])[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Br:12]>>[Br:12][CH2:11][C:10]1[CH:9]=[C:8]([O:7][C:6]([F:5])([F:16])[F:17])[CH:15]=[CH:14][C:13]=1[N+:1]([O-:4])=[O:2]

Komponenten

3

Edukt 2

HCID 944Nitric AcidHCID 7371761-(Bromomethyl)-3-(trifluoromethoxy)benzene

Produkt 1

HCID 667165912-Nitro-5-(trifluoromethoxy)benzyl bromide

Versuchsvorschrift

Fuming nitric acid (5 mL) was cooled to 0° C. and 3-(trifluoromethoxy)benzyl bromide (1 mL, 6.16 mmol) was added. After 15 minutes, the reaction was poured into ice water (100 mL) and extracted with EtOAc (200 mL). The organic layer was washed with water, saturated NaHCO3, and brine (75 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes) afforded 2-(bromomethyl)-1-nitro-4-(trifluoromethoxy)benzene Rf=0.54 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.14 (d, J=8.9 Hz, 1H), 7.43 (m, 1H), 7.31 (m, 1H), 4.82 (s, 2H).

Aufarbeitung

  1. extractionextracted with EtOAc (200 mL)
  2. washThe organic layer was washed with water, saturated NaHCO3, and brine (75 mL each)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography on silica gel (0 to 15% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5abadb369efb4bc9a684d7126d5d877b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781426B2

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