1,2-Dibromoethane → HCID 59216374, compound

HRID 41907Notes

Reaction equation

HRID 41907 reaction equation
O.[Na].[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][C:21]#[N:22])[CH:16]=3)[C:11]2=[O:23])=[CH:7][CH:6]=1.Br[CH2:27][CH2:28]Br.C(OC(=O)C)C>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]4([C:21]#[N:22])[CH2:28][CH2:27]4)[CH:16]=3)[C:11]2=[O:23])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 59216379HCID 59216379, compoundHCID 71353970Sodium monohydrate2×

Product 1

HCID 59216374HCID 59216374, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydrate (0.228 g, 60%, 5.72 mmole) in 15 ml DMF was added nitrile (IV) (1.2 g, 3.9 mmole ) and after stirring for 15 minutes at room temperature 1,2-dibromo-ethane (1.1 g, 5.8 mmole ) in 1.5 ml DMF was added. The resulting mixture was stirred 0.5 hour at room temperature and then more sodium hydrate (0.114 g, 2.86 mmole ) was added and the reaction mixture heated for about 10 minutes at 30-35° C. After cooling the mixture was partitioned between ethylacetate and brine, the organic layer was dried over sodium acetate and concentrated in vacuo. Purification by silica gel column chromatography with 30% -50% ethylacetate in hexane afforded compound (V ) 1 g (77% yield).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture heated for about 10 minutes at 30-35° C
  3. temperatureAfter cooling the mixture
  4. customwas partitioned between ethylacetate and brine
  5. dry with materialthe organic layer was dried over sodium acetate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f49391863394a5b9c1ec16952c97f97
Source dataset
uspto-grants-2013_09
Patent number
US08536166B2

Reaction notes

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