1,2-Dibromoethane → HCID 14180572, compound

HRID 1904962Notes

Reaction equation

HRID 1904962 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([OH:13])=[C:6]([OH:14])[C:5]2=[O:15].[H-].[Na+].Br[CH2:19][CH2:20]Br>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]1[O:13][CH2:19][CH2:20][O:14][C:6]=1[C:5]2=[O:15]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 1356252826-chloro-2,3-dihydroxy-1,4-naphthoquinone

Product 1

HCID 14180572HCID 14180572, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Chloro-2,3-dihydroxy-1,4-naphthoquinone (11.25 g) dissolved in dry dimethylformamide (100 ml) is treated with washed sodium hydride (2.64 g) in small portions under a blanket of nitrogen. After stirring 1 hour at room temperature, 1,2-dibromoethane (4.3 ml) is added via a syringe over 1 hour. The resultant mixture is warmed to 60° C. overnight, then cooled and diluted with water (500 ml) to afford 6-chloro-2,3-ethylenedioxy-1,4-naphthoquinone.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-a5c92d6066c0466d8cc8fb2bc723559b
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

Loading…