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

HRID 1040381

반응식

HRID 1040381 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 38498355-(Benzyloxy)-2-nitrobenzaldehyde

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ecea00dc8af24c10a89f28789974b9a3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552220B2

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