Allyl bromide → 3-Chloro-4-(prop-2-en-1-yloxy)benzaldehyde

HRID 38718

반응식

HRID 38718 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C=O)C.C1COCC1.O>[CH2:15]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Cl:1])[CH:14]=[CH2:13]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 24758Sodium hydride

생성물 1

HCID 47700363-Chloro-4-(prop-2-en-1-yloxy)benzaldehyde수율 85.6%

시약·촉매·용매 2

HCID 962Water용매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

To a solution of 3-chloro-4-hydroxybenzaldehyde (5.0 g, 31.9 mmol) in DMF/THF 1:3 (120 mL) is added NaH (1.67 g of a 55% dispersion in mineral oil, 38.3 mmol) in four portions. The mixture is stirred at rt for 1 h before allylbromide (9.66 g, 79.8 mmol) is added. The reaction mixture is heated to 65° C. for 18 h, diluted with water (250 mL) and extracted with diethyl ether (3×250 mL). The organic extracts are washed with water (250 mL), combined and concentrated. The remaining oil is chromatographed on silic gel with heptane/EA 4:1 to afford 4-allyloxy-3-chlorobenzaldehyde (5.37 g) as an almost colourless oil. LC: tR=0.95 min.

후처리

  1. additionis added
  2. extractionextracted with diethyl ether (3×250 mL)
  3. washThe organic extracts are washed with water (250 mL)
  4. concentrationconcentrated
  5. customThe remaining oil is chromatographed on silic gel with heptane/EA 4:1

출처 및 근거

ORD 기록
ord-482bcd3dcc48433ea236a8b74dc6f9fd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524752B2

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