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

HRID 1028595노트

반응식

HRID 1028595 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-97ea0450d4cc4d03b75bc64953c9424a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735435B2

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