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

HRID 1040386ノート

反応式

HRID 1040386 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 108700245-(Benzyloxy)-2-bromobenzaldehyde収率 97%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f03e115501574fd19195461440c439df
出典データセット
uspto-grants-2013_10
特許番号
US08552220B2

反応ノート

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