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

HRID 503239노트

반응식

HRID 503239 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
30 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1c72c2d20b3f4116952a3082e457110c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

반응 노트

불러오는 중…