Water → HCID 58183192, compound

HRID 468284Notes

Reaction equation

HRID 468284 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([F:12])[C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=1.[C-:13]#[N:14].[Na+].O>CS(C)=O>[F:12][C:5]1[C:6]2[O:10][CH2:9][O:8][C:7]=2[CH:11]=[C:3]([CH2:2][C:13]#[N:14])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 591293256-(Chloromethyl)-4-fluorobenzo[d][1,3]dioxole

Product 1

HCID 58183192HCID 58183192, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 6-chloromethyl-4-fluoro-benzo[1,3]dioxole (0.80 g, 4.3 mmol) and NaCN (417 mg, 8.51 mmol) in DMSO (20 mL) was stirred at 30° C. for 1 h and was 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 (petroleum ether/ethyl acetate=10/1) to afford 2-(7-fluorobenzo[d][1,3]dioxol-5-yl)acetonitrile (530 mg, 70%). 1H NMR (300 MHz, CDCl3) δ 6.68-6.64 (m, 2H), 6.05 (s, 2H), 3.65 (s, 2H). 13C-NMR 8151.1, 146.2, 134.1, 124.2, 117.5, 110.4, 104.8, 102.8, 23.3.

Workup

  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 (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-46b30560726448bfb2f4202ef08ec2c5
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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