Water → (6-Fluoro-benzo[1,3]dioxol-5-yl)-acetonitrile

HRID 468247ノート

反応式

HRID 468247 の反応式
Cl[CH2:2][C:3]1[C:11]([F:12])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[C-:13]#[N:14].[Na+].O>CS(C)=O>[F:12][C:11]1[C:3]([CH2:2][C:13]#[N:14])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 591292085-Chloromethyl-6-fluoro-benzo[1,3]dioxole

生成物 1

HCID 67044109(6-Fluoro-benzo[1,3]dioxol-5-yl)-acetonitrile収率 87%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
30 °C

実験手順

A mixture of 5-chloromethyl-6-fluoro-benzo[1,3]dioxole (640 mg, 3.4 mmol) and NaCN (340 mg, 6.8 mmol) in DMSO (20 mL) was stirred at 30° C. for 1 h and then poured into water. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2SO4, and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford (6-fluoro-benzo[1,3]dioxol-5-yl)-acetonitrile (530 mg, 70%). 1H-NMR (300 MHz, CDCl3) δ 6.82 (d, J=4.8, 1H), 6.62 (d, J=5.4, 1H), 5.99 (s, 2H), 3.65 (s, 2H).

後処理

  1. extractionThe mixture was extracted with EtOAc (50 mL×3)
  2. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customto give the crude product, which
  6. customwas purified by column chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-b4407a92a71c48f3bd41e3c05313ad40
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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