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

HRID 2037860Notes

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]=1

Participants

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-63493ff9a07b42ddab08bb427a60c9d5
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575209B2

Reaction notes

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