1-Bromo-2-Chloroethane → HCID 11118001, compound

HRID 1166723Notes

Reaction equation

HRID 1166723 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][Cl:23]>CN(C)C=O.C(OCC)(=O)C>[Cl:23][CH2:22][CH2:21][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 11118001HCID 11118001, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxy-1-naphthaldehyde (8.6 g, 50 mmoles) and potassium carbonate (13.8 g, 100 mmoles) in N,N-dimethylformamide (DMF)(40 mL) was added 1-bromo-2-chloroethane (7.4 g, 50 mmoles). The mixture was heated at 60° C. overnight. The solution was diluted with ethyl acetate (500 mL), extracted with water and brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated to obtain 12.1 g product (52% yield).

Workup

  1. extractionextracted with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-525c7252905f4f4c9ed383bc55e8b4cf
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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