Water → (3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile

HRID 1835996노트

반응식

HRID 1835996 반응식
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH2:10]Cl)[C:3]=1[O:12][CH3:13].[C-:14]#[N:15].[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:10][C:14]#[N:15])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 9032Potassium CyanideHCID 103081541-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

생성물 1

HCID 10149238(3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile수율 77%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene 53 (7.0 g, 26.4 mmol) and KCN (1.7 g, 26.4 mmol) in DMSO (50 ml) was heated to 75° C. After 2 hr, the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc and the organic layer was dried and concentrated. The product was purified by column chromatography on silica gel (20% EtOac/Hex) to give 54 as an oil (5.2 g, 77%): 1H NMR (DMSO-d6) δ 7.20 (d, 1 H, J=3.0 Hz), 6.99 (d, 1 H, J=3.0 Hz), 4.00 (s, 2 H), 3.75 (s, 6 H)

후처리

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography on silica gel (20% EtOac/Hex)

출처 및 근거

ORD 기록
ord-ff088186f6264dc9a81d033c904adf55
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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