N-bromobutanimide → HCID 17829551, compound

HRID 645308Notes

Reaction equation

HRID 645308 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Br:21]N1C(=O)CCC1=O>C(Cl)Cl.S(=O)(=O)(O)O>[CH2:19]([O:18][C:16]([C:9]1[C:10]2[C:15](=[CH:14][C:13]([Br:21])=[CH:12][CH:11]=2)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)=[O:17])[CH3:20]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 114486561,4-Diethyl 1,4-naphthalenedicarboxylate

Product 1

HCID 17829551HCID 17829551, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Naphthalene-1,4-dicarboxylic-acid diethyl ester 35.0 g was dissolved in a mixed solvents 280 ml of methylene chloride and concentrated sulfuric acid (weight ratio 3:7), and N-bromo succinimide 22.9 g was added here at a room temperature. After stirring overnight, the reaction mixture was poured into ice, and extracted with ethyl acetate. The extracted solution was washed with diluted alkaline water, subsequently with water, and then dried by magnesium sulfate. The solution was concentrated, and treaded with column processing (silica gel/chloroform), and 28.0 g of a crude product of 6-bromonaphthalene-1,4-dicarboxylic-acid diethyl ester was obtained.

Workup

  1. additionwas added here at a room temperature
  2. additionthe reaction mixture was poured into ice
  3. extractionextracted with ethyl acetate
  4. washThe extracted solution was washed
  5. additionwith diluted alkaline water
  6. dry with materialsubsequently with water, and then dried by magnesium sulfate
  7. concentrationThe solution was concentrated
  8. customwas obtained

Sources & evidence

ORD record
ord-5cfd346cf1654b11b21fd5a4140c18c0
Source dataset
uspto-grants-2010_04
Patent number
US07701129B2

Reaction notes

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