Water → 2-(4-Bromo-2-methylphenyl)acetonitrile

HRID 603129노트

반응식

HRID 603129 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH3:10])[CH:3]=1.[C-:11]#[N:12].[Na+].O.C([O-])(O)=O.[Na+]>CN(C=O)C.CCCCCC.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]#[N:12])=[C:4]([CH3:10])[CH:3]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

생성물 1

HCID 184142962-(4-Bromo-2-methylphenyl)acetonitrile수율 93%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584099Diethylether hexane용매

반응 조건

온도
2.5 °C

실험 절차

1-Bromo-4-(bromomethyl)-3-methylbenzene (13.2 g, 50.1 mmol) is dissolved in DMF (65 mL). The reaction mixture is cooled to 0-5° C. and NaCN (3.66 g, 74.6 mmol) is added follow by water (8 mL). The reaction is stirred overnight at room temperature and water (170 mL) is added followed by NaHCO3 sat. (130 mL) and hexane/Et2O (2:1) (150 mL). The organic phase is separated and the aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL). The combined organic phases are washed with water (170 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-2-methylphenyl)acetonitrile (9.76 g, 93%) as an orange oil. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.40-7.32 (2H, m), 7.23 (2H, d, J=8.2 Hz), 3.61 (2H, s), 2.32 (3H, s).

후처리

  1. customThe organic phase is separated
  2. extractionthe aqueous phase extracted with hexane/Et2O (2:1) (3×150 mL)
  3. washThe combined organic phases are washed with water (170 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-482d97157f1946ee8db1915ea869143a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906654B2

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