Water → 2-(4-Fluoronaphthalen-1-yl)acetonitrile

HRID 8212노트

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HRID 8212 반응식
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([F:13])=[CH:5][CH:4]=1.[C-:14]#[N:15].[Na+].O>CN(C)C=O>[F:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH2:2][C:14]#[N:15])=[CH:4][CH:5]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 156574171-(Chloromethyl)-4-fluoronaphthalene

생성물 1

HCID 219925322-(4-Fluoronaphthalen-1-yl)acetonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A solution of 1-chloromethyl-4-fluoronaphthalene (5.45 g, 5.66 mmol), sodium cyanide (333 mg, 6.79 mmol), and water (2 mL) in N,N-dimethylformamide (30 mL) is stirred for 8 h, then heated at 70° C. for 15 h. The mixture is cooled to room temperature and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic portion is washed with three portions of water, one portion of brine, dried (sodium sulfate), filtered and evaporated. The residue is chromatographed on SiO2 (30% ethyl acetate/hexane) to yield the title compound, 4.67 g (90%), as a light brown solid. 1H NMR (CDCl3): δ 8.19 (d, J=8 Hz, 1H), 7.87 (d, J=8 Hz, 1H), 7.68 (ddd, J=8, 7, 1 Hz, 1H), 7.63 (ddd, J=8, 7, 1 Hz, 1H), 7.51 (dd, J=8, 5 Hz, 1H), 7.14 (dd, J=10, 8 Hz, 1H), 4.09 (s, 2H).

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. washThe organic portion is washed with three portions of water, one portion of brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-fd8e422ad9204a379e007b50fb4602f2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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