1,1-Dibromoethane → HCID 10584444, compound

HRID 912425Notes

Reaction equation

HRID 912425 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[OH:12])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:21](Br)[CH3:22]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[O:12][CH2:21][CH2:22][NH:11][C:7]=2[CH:8]=[CH:9][CH:10]=1)=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 22096614Ethyl 3-amino-2-hydroxybenzoate

Product 1

HCID 10584444HCID 10584444, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl ester 3.6 g (20 mmol) of step 2 in dimethylformamide 30 mL was added K2CO3 5.5 g (40 mmol), followed by stirring at room temperature for 10 min. Dibromoethane 1.9 mL (22 mmol) was added dropwise to the reaction mixture which was then stirred for 3 hours under reflux. The reaction mixture was cooled to room temperature, concentrated in a vacuum, diluted with ethylacetate, and washed with a saturated sodium bicarbonate solution and a saturated NaCl solution. The resulting residue was dried over magnesium sulfate and concentrated in a vacuum to afford 3.7 g of the title compound (yield 89%).

Workup

  1. stirringwas then stirred for 3 hours
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated in a vacuum
  5. additiondiluted with ethylacetate
  6. washwashed with a saturated sodium bicarbonate solution
  7. dry with materialThe resulting residue was dried over magnesium sulfate
  8. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-3abb101189024ef19a942e1b658ae48f
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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