Water → 2-(Benzyloxy)-5-fluorobenzaldehyde

HRID 2036234노트

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HRID 2036234 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27373285-Fluorosalicylaldehyde

생성물 1

HCID 107281542-(Benzyloxy)-5-fluorobenzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 5-fluoro-2-hydroxybenzaldehyde (5.0 g, 35.69 mmol, 1.00 eq.) and potassium carbonate (7.97 g, 57.10 mmol, 1.60 eq.) in DMF (60 mL), benzyl bromide (4.54 mL, 37.47 mmol, 1.05 eq.) was added dropwise. The reaction mixture was refluxed for 2 hours, then allowed to cool to r.t. and poured into 100 mL of cold water and extracted with AcOEt. The organic extract was washed with 10% aq. NaOH soln. and sat. aq. NaCl soln., dried over MgSO4 and concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+30% AcOEt) to yield 2-benzyloxy-5-fluoro-benzaldehyde as an yellow oil.

후처리

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. extractionextracted with AcOEt
  4. extractionThe organic extract
  5. washwas washed with 10% aq. NaOH soln
  6. dry with material, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+30% AcOEt)

출처 및 근거

ORD 기록
ord-d512ea9b9df74892a4f158454a29287d
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575158B2

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