1-Bromooctane → HCID 22603581, compound

HRID 2307949Notes

Reaction equation

HRID 2307949 reaction equation
[I:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([I:15])=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C>[CH2:23]([N:5]1[C:6]2[CH:7]=[C:8]([I:15])[CH:9]=[CH:10][C:11]=2[C:12]2[C:4]1=[CH:3][C:2]([I:1])=[CH:14][CH:13]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 22603576HCID 22603576, compound

Product 1

HCID 22603581HCID 22603581, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 5 (3.00 g) in 30 mL of anhydrous DMF was added 660 mg (4.78 mmol, Aldrich Co.) of anhydrous K2CO3. The solution was stirred at 80° C. for 2 h under argon after 0.93 g (4.82 mmol) of bromooctane was added. The mixture was stirred at 80° C. for 24 h and then quenched with 30 mL of water. The aqueous layer was extracted three times with 50 mL of diethyl ether. The organic layer was dried over magnesium sulfate and the solvent was removed under vacuum. The residue was purified by column chromatography (silica gel, hexanes as eluent) followed by recristallization in methanol to give 1.55 g of the title product as a white solid. M.P. 82-84° C. (Global yield for the last two steps: 38%).

Workup

  1. additionwas added
  2. customquenched with 30 mL of water
  3. extractionThe aqueous layer was extracted three times with 50 mL of diethyl ether
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe residue was purified by column chromatography (silica gel, hexanes as eluent)

Sources & evidence

ORD record
ord-d8f52518922a4b5188f8292cb393ae34
Source dataset
uspto-grants-2004_12
Patent number
US06833432B2

Reaction notes

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