Water → 2-{[(3-Chloro-4-fluorophenyl)thio]methyl}pyridine

HRID 1686471Notes

Reaction equation

HRID 1686471 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Cl.[Cl:10][C:11]1[CH:12]=[C:13]([SH:18])[CH:14]=[CH:15][C:16]=1[F:17].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([S:18][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 27341973-Chloro-4-fluorobenzene-1-thiol

Product 1

HCID 689560522-{[(3-Chloro-4-fluorophenyl)thio]methyl}pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Picolyl chloride hydrochloride (3.03 g) was added to a stirred suspension of 3-chloro-4-fluorobenzenethiol (3.0 g) and cesium carbonate (12.0 g) in DMF (50 ml) and the mixture stirred at RT overnight. Mixture poured into water, organics extracted into ether and the ether extracts washed (brine), dried (MgSO4) and evaporated under reduced pressure to a green oil (4.0 g).

Workup

  1. extractionorganics extracted into ether
  2. washthe ether extracts washed (brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure to a green oil (4.0 g)

Sources & evidence

ORD record
ord-28cd284ea8cb470399a3001344abcd9f
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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