2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 354336

反応式

HRID 354336 の反応式
[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

参加物

6

反応物 3

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

生成物 1

HCID 736266Benzyl 2-nitrophenyl ether収率 89.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e93681dbdb274ed0aab40efb3ceb94ec
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

関連ノート

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