Water → 2-(Benzylsulfanyl)-5-bromopyridine

HRID 130420Notes

Reaction equation

HRID 130420 reaction equation
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[CH:14][C:15](Cl)=[N:16][CH:17]=1.O>CN(C)C=O.C(OCC)(=O)C>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([S:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 550290752-(Benzylsulfanyl)-5-bromopyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of phenylmethanethiol (1 ml, 8 mmol) in N,N-dimethylformamide (15 ml) under an atmosphere of argon was treated with sodium hydride (352 mg, 8.8 mmol, 60% dispersion in oil). After stirring at room temperature for 15 minutes a solution of 5-bromo-2-chloropyridine (1.84 g, 9.6 mmol) in N,N-dimethylformamide (5 ml) was added. After 2 hours, water and ethyl acetate were added. The organic layer was separated and washed with water, brine and dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was then purified by chromatography on silica gel eluting with 5% ethyl acetate in pentane to give the title compound. MS (ES+) 280/282 [M+H]+.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by chromatography on silica gel eluting with 5% ethyl acetate in pentane

Sources & evidence

ORD record
ord-6017d3ec9b5f44bd93f90d7d9ba39a45
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

Loading…