1-Bromo-3-chloropropane → HCID 11609638, compound

HRID 1786444Notes

Reaction equation

HRID 1786444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[N:11]([CH3:16])[C:12]([SH:15])=[N:13][CH:14]=2)[OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>CC(C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[N:11]([CH3:16])[C:12]([S:15][CH2:24][CH2:25][CH2:26][Cl:27])=[N:13][CH:14]=2)[OH:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178481122HCID 178481122, compound

Product 1

HCID 11609638HCID 11609638, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Example I, Step A (0.09 g) in acetone (2 mL) and DMF (2 mL) was treated with K2CO3 (0.2 g) followed by 1-bromo-3-chloropropane (0.11 g). The mixture was allowed to stir at rt for 16 h and was then partitioned between EtOAc (50 mL) and brine (50 mL). The organic layer was separated and washed with brine (2×200 mL), dried over Na2SO4, filtered, and evaporated to give the crude product. The crude product was purified by silica gel chromatography using 2-5% MeOH/CH2Cl2 as the eluent to provide (4-Chloro-phenyl)-[2-(3-chloro-propylsulfanyl)-3-methyl-3H-imidazol-4-yl]-methanol (0.08 g, 69%); M calc=330; M+H found=331.

Workup

  1. customwas then partitioned between EtOAc (50 mL) and brine (50 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (2×200 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-517acf81c55344f99fba65175862b982
Source dataset
uspto-grants-2009_03
Patent number
US07507756B2

Reaction notes

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