1,1-Dichloroethane → HCID 22315883, compound

HRID 1851664Notes

Reaction equation

HRID 1851664 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1)[CH3:2].ClC(Cl)C.[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>CO>[Br:23][CH:1]([C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 6547AzobisisobutyronitrileHCID 67722-EthylanthraquinoneHCID 67184N-bromobutanimide

Product 1

HCID 22315883HCID 22315883, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To the solution dissolved 15.0 g of 2-ethylanthraquinone (63 mmol; produced by Wako Pure Chemical Industries, Ltd.) into 100 mL of dichloroethane, 11.3 g of N-bromosuccinimide (NBS) (63.5 mmol; produced by Wako Pure Chemical Industries, Ltd.) and 1.0 g of 2,2′-azobis(isobutyronitrile) (AIBN) (6.1 mmol; produced by Wako Pure Chemical Industries, Ltd.) were added, then, the solution was reacted by stirring for 2 hours at 60° C. After completing reaction, the reaction solution was condensed, and 120 mL of methanol was poured into the condensed residue, and after the resultant crystal was filtered, the resultant crystal was dried to obtain 18.0 g of 2-(1-bromo-1-ethyl)anthraquinone (yield: 90%) as pale yellow crystal. Measurement results of 1H-NMR are shown as the follows:

Workup

  1. additionwere added
  2. customthe solution was reacted
  3. customreaction
  4. additionwas poured into the condensed residue
  5. filtrationafter the resultant crystal was filtered
  6. customthe resultant crystal was dried

Sources & evidence

ORD record
ord-8f498e887de64ea8a505dd92bda9942c
Source dataset
uspto-grants-2015_02
Patent number
US08957212B2

Reaction notes

Loading…