Water → (6-Fluoro-benzo[1,3]dioxol-5-yl)-acetonitrile
Reaction equation
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
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, 1 H), 6.62 (d, J=5.4, 1 H), 5.99 (s, 2 H), 3.65 (s, 2 H).
Workup
- extractionThe mixture was extracted with EtOAc (50 mL×3)
- washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customto give the crude product, which
- customwas purified by column chromatography on silica gel (5-10% ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-d982b630ada44c259e270a37a2245d65
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415387B2
Reaction notes
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