Sodium hydride → HCID 118307834, compound

HRID 718364Notes

Reaction equation

HRID 718364 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1>C1COCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 118307834HCID 118307834, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenyl)ethanol (0.568 g) in THF (10 mL) was added NaH (0.270 g, 60% in oil). The mixture was stirred at room temperature for 2 hours, before 2,5-dibromopyridine (0.8 g) was added. The mixture was stirred at room temperature for 16 h. The reaction was quenched with water and extracted with EtOAc (2×20 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by silica gel column (Hex/EtOAc=100:5) to give 5-bromo-2-(4-fluorophenethoxy)pyridine (0.3 g). LCMS (M+H)=296.0.

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel column (Hex/EtOAc=100:5)

Sources & evidence

ORD record
ord-a8df3d650200480183a3fe10aed9421d
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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