1,2-Dibromoethane → HCID 59216374, compound

HRID 2069800Notes

Reaction equation

HRID 2069800 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-91ad76fd012c4d9a8a94902dfc67e81e
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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