1,2-Dibromoethane → HCID 67426891, compound

HRID 2235342Notes

Reaction equation

HRID 2235342 reaction equation
[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=[O:15])[CH2:2][CH2:3][CH2:4][CH3:5].Br[CH2:17][CH2:18]Br.[H-].[Na+].[NH4+].[Cl-]>CN(C)C=O.CO>[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:18][CH2:17]2)[C:7]1=[O:15])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12383454HCID 12383454, compound

Product 1

HCID 67426891HCID 67426891, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 1-pentyl-1,3-dihydro-indol-2-one (Farmaco, Ed. Sci. 1977, 32, 703-712) (22 g) and 1,2-dibromoethane (14.1 ml; 162 mmol) in dry N,N-dimethylformamide (180 ml) is added sodium hydride (60% in mineral oil, 13 g; 325 mmol) in small portions over a period of 15 min. The resulting mixture is stirred at 15° C. for 1 h. MeOH (50 ml) and saturated NH4Cl solution (200 ml) is added and the aqueous phase is extracted with Et2O. The combined organic layer is washed with water, brine and dried over MgSO4. The compound (24.8 g) is obtained after evaporation.

Workup

  1. extractionthe aqueous phase is extracted with Et2O
  2. washThe combined organic layer is washed with water, brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d4069c13b37c44838b1c203601bfcd83
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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