Bromine → HCID 22625622, compound

HRID 277661Notes

Reaction equation

HRID 277661 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[CH:17]=1.[Br:18]Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:18][C:17]1[N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:11]2=[N:10][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 22625614HCID 22625614, compound

Product 1

HCID 22625622HCID 22625622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 0.8 g (3.0 mmol) of the above 2-(2,4-dichlorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine stirring in 50 ml of methylene chloride at room temperature, 0.5 g (3.1 mmol) of bromine in 5 ml of methylene chloride was added dropwise. The solution was stirred for 2 h. Another 20 ml of methylene chloride and excess saturated aqueous sodium bicarbonate were added. After sufficient mixing, the methylene chloride layer was separated, washed with water and brine, and dried over magnesium sulfate. Evaporating the solvent in vacuo gave a yellow solid residue which was purified by silica gel column chromatography (5:1 followed by 3:1 followed in turn by 1:1 hexane/ethyl acetate) to yield a 0.55 g sample of the title compound (m.p. 112-113° C.).

Workup

  1. customAfter sufficient mixing, the methylene chloride layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporating the solvent in vacuo
  5. customgave a yellow solid residue which
  6. customwas purified by silica gel column chromatography (5:1 followed by 3:1 followed in turn by 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-80822178445a4ad2bd1c98cabb2e3a7e
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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