Water → 2-(5-Bromo-2-fluorophenyl)acetonitrile

HRID 563787Notes

Reaction equation

HRID 563787 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9]Br)[CH:3]=1.[C-:11]#[N:12].[Na+].CCOC(C)=O.O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][C:11]#[N:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 235096312-(5-Bromo-2-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromo-2-bromomethyl-1-fluoro-benzene (1.2 g, 3.7 mmol) and sodium cyanide (2.0 g, 4.1 mmol) were combined in DMSO (15 mL) and stirred at 90° C. for 2 hours. Once no starting material was seen by analytical tlc, the mixture was worked-up with EtOAc and H2O to give the title compound.

Sources & evidence

ORD record
ord-d5aa4535bafa47a2ac585db95af5ff5a
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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