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

HRID 1040386노트

반응식

HRID 1040386 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)C>[CH2:17]([O:10][C:7]1[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([CH:6]=1)[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehyde

생성물 1

HCID 108700245-(Benzyloxy)-2-bromobenzaldehyde수율 97%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 2-bromo-5-hydroxybenzaldehyde (100 mg, 0.50 mmol), potassium carbonate (138 mg, 1.00 mmol), and tetrabutylammonium iodide (18 mg, 0.05 mmol) in 1.0 mL of dry N,N-dimethylformamide was added benzyl bromide (89 μL, 0.74 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was diluted with diethyl ether. 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=95/5 to 80/20) to obtain the title compound as a colorless oil (140 mg, 97%).

후처리

  1. washThe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

출처 및 근거

ORD 기록
ord-f03e115501574fd19195461440c439df
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552220B2

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