2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 354336

반응식

HRID 354336 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH2:17]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

생성물 1

HCID 736266Benzyl 2-nitrophenyl ether수율 89.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2-nitrophenol (10.0 g, 72.0 mmol) and K2CO3 (9.96 g, 72.0 mmol) in DMF (150 mL) was added dropwise benzyl bromide (9.40 mL, 79.2 mmol) at 0° C. After being stirred at room temperature for 3 hr, the reaction mixture was diluted with water, which was extracted with Et2O. The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with hexane-EtOAc (2:1, v/v) as eluent gave 2-benzyloxy nitrobenzene (14.7 g, 89%) as a yellow oil. 1H-NMR (CDCl3) δ5.24 (s, 2H), 7.04 (t, J=7.8 Hz, 1H), 7.12 (d, J=7.8 Hz, 1H), 7.31-7.50 (m, 5H), 7.51 (d, J=1.5 Hz, 1H), 7.86 (dd, J=7.8, 1.5 Hz, 1H).

후처리

  1. extractionwas extracted with Et2O
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-e93681dbdb274ed0aab40efb3ceb94ec
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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