4-Bromophenol → 2-(4-bromophenoxy)acetonitrile

HRID 746764Notes

Reaction equation

HRID 746764 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]#[N:18]>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][C:17]#[N:18])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 5988232-(4-bromophenoxy)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Mix 4-bromophenol (1.4 mmol) in acetonitrile (5 ml) and water (2 ml), add K2CO3 (3 mmol) and bromoacetonitrile (1.5 mmol) at room temperature under inert atmosphere. Heat the mixture to 80° C. for 16 h. Analyze by LC/MS for final product. Evaporate the solvent and add water. Extract product with DCM (3×) and combine and evaporate organic phases to afford the title compound.

Sources & evidence

ORD record
ord-659934e18058415dbe29df353dd54d6c
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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