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

HRID 8212ノート

反応式

HRID 8212 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fd8e422ad9204a379e007b50fb4602f2
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

反応ノート

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