Benzyl Bromide → 5-(Benzyloxy)-2-nitrobenzaldehyde

HRID 1040381

反応式

HRID 1040381 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

生成物 1

HCID 38498355-(Benzyloxy)-2-nitrobenzaldehyde

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol), potassium carbonate (498 mg, 3.60 mmol), and tetrabutylammonium iodide (66 mg, 0.18 mmol) in 1.8 mL of dry N,N-dimethylformamide was added benzyl bromide (0.32 mL, 2.7 mmol) at 0° C. After being stirred at room temperature until the starting material disappeared (5 h), the reaction mixture was filtered to remove inorganic salts. The filtrate was diluted with diethyl ether, and the solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain the title compound as a slightly yellow solid (405 mg, 87%).

後処理

  1. custom(5 h)
  2. filtrationthe reaction mixture was filtered
  3. customto remove inorganic salts
  4. additionThe filtrate was diluted with diethyl ether
  5. washthe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

出典と根拠

ORDレコード
ord-ecea00dc8af24c10a89f28789974b9a3
出典データセット
uspto-grants-2013_10
特許番号
US08552220B2

関連ノート

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