Sodium hydride → HCID 59233267, compound

HRID 1925172Notes

Reaction equation

HRID 1925172 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[H-].[Na+].Br[CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 59233267HCID 59233267, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-2-hydroxybenzonitrile (1 g, 5.05 mmol) in DMF was treated with 95% NaH (242 mg, 9.6 mmol) for 20 min at room temperature. 2-(2-Bromoethoxy)tetrahydro-2H-pyran (0.839 ml, 5.56 mmol) was then added to the reaction and the mixture was stirred at room temperature for 5 hrs. The reaction was then diluted with DCM and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated to dryness to provide the crude title compound, 5-bromo-2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)benzonitrile (1.6 g, 9.75% yield) which was used without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-08a74c9b35ad476389a7ff44765a884f
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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