Bromine → HCID 57466726, compound

HRID 1875347Notes

Reaction equation

HRID 1875347 reaction equation
[CH3:1][CH:2]1[N:7]([CH3:8])[CH2:6][C:5]2[S:9][CH:10]=[CH:11][C:4]=2[CH2:3]1.FC(F)(F)C([O-])=O.[Br-:19].[K+].BrBr>O>[Br:19][C:10]1[S:9][C:5]2[CH2:6][N:7]([CH3:8])[CH:2]([CH3:1])[CH2:3][C:4]=2[CH:11]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 84468TrifluoroacetateHCID 253877Potassium BromideHCID 57423980HCID 57423980, compound

Product 1

HCID 57466726HCID 57466726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.0 g (3.6 mmol) 5,6-dimethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine (as the trifluoroacetate salt) are dissolved in 60 ml of water and at the temperature of an ice bath combined with a solution of 1.0 g (8.5 mmol) potassium bromide and 182 μl (3.6 mmol) bromine in 20 ml of water. The mixture is stirred for 2.5 hours in the ice bath and then extracted twice with 100 ml ethyl acetate. The combined organic phases are washed with sat. sodium chloride solution, then dried on sodium sulphate and evaporated down i. vac. The crude product thus obtained is purified by chromatography on silica gel (eluant DCM/methanol 50:1).

Workup

  1. extractionextracted twice with 100 ml ethyl acetate
  2. washThe combined organic phases are washed with sat. sodium chloride solution
  3. customdried on sodium sulphate
  4. customevaporated down i

Sources & evidence

ORD record
ord-022e953da41749cfa28ff4b5d96536dc
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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