Diethyl Ether → HCID 18184310, compound

HRID 1358240Notes

Reaction equation

HRID 1358240 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[C:10]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=2[O:8][CH:7]=1.C(OCC)C>CS(C)=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]2[O:8][CH:7]=[C:6]([CH2:5][C:1]#[N:2])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 181843143-(Chloromethyl)-5-fluorobenzofuran

Product 1

HCID 18184310HCID 18184310, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of sodium cyanide (10 g) in dimethylsulfoxide (150 mL) was heated to 80° C. followed by quick addition of a solution of 3-chloromethyl-5-fluorobenzofuran (10 g) in dimethylsulfoxide (50 mL). The mixture was kept at 80° C. for ½ h and then poured onto ice. Standard work-up with diethyl ether gave a dark crystalline material, 5-fluorobenzofuran-3-ylacetonitrile (8.8 g).

Workup

  1. additionpoured onto ice

Sources & evidence

ORD record
ord-d6fa03600dab41d1bb574695d849522f
Source dataset
uspto-grants-2003_07
Patent number
US06596722B2

Reaction notes

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