Ethyl Acetate → (8-Fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)acetonitrile

HRID 253304Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:4]=[C:5]([F:13])[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[CH:12]=1.[C-:14]#[N:15].[K+].C(OCC)(=O)C>CN(C=O)C>[F:13][C:5]1[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[CH:12]=[C:3]([CH2:2][C:14]#[N:15])[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 7-(chloromethyl)-5-fluoro-2,3-dihydro-1,4-benzodioxine (0.92 g, 4.55 mmol) and potassium cyanide (1.55 g, 23.8 mmol) in DMF (10 mL) was stirred at 60° C. for 18 h. After cooling to rt ethyl acetate (100 mL) was added and the mixture was washed with water (2×30 mL) then brine (30 mL) and dried over sodium sulfate. Filtration and concentration followed by column chromatography on silica (4:1 hexanes/ethyl acetate) afforded (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)acetonitrile (0.42 g, 46% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 6.61 (m, 2H), 4.30 (s, 4H), 3.62 (s, 2H)

Workup

additionwas added
washthe mixture was washed with water (2×30 mL)
dry with materialbrine (30 mL) and dried over sodium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-f6597a94a47745458f0eeab0eac87f92
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872014B2

Reaction notes

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