2,5-Dibromopyridine → 5-Bromo-2-(methylthio)pyridine

HRID 2103645Notes

Reaction equation

HRID 2103645 reaction equation
[CH3:1][S-:2].[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][N:6]=1>CN(C=O)C.O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([S:2][CH3:1])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 693532,5-DibromopyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 114242515-Bromo-2-(methylthio)pyridineYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add sodiumthiomethoxide (1.0 g, 14.4 mmol) to a suspension of 2,5-dibromo-pyridine (3.1 g, 13 mmol) in DMF (8 ml) at r.t. Stir for 2 h at r.t., dilute with water (20 ml) and extract 2 times with MTBE. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 2.59 g of 5-bromo-2-methylsulfanyl-pyridine. MS (m/e): 205 (M+H).

Workup

  1. extractionextract 2 times with MTBE
  2. customDry organic layers over sodium sulfate and remove solvents under vacuum

Sources & evidence

ORD record
ord-0dbe840ae65a4e58a4a4514b2dfd818f
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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