1,1-Dibromoethane → HCID 178492974, compound

HRID 2186527Notes

Reaction equation

HRID 2186527 reaction equation
[Mg:1].BrC(Br)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[C:10]([O:15][CH3:16])[C:9]=1[O:17][CH3:18].[Br-:19].C1COCC1>C1COCC1.[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2]>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([Mg:1][Br:19])[CH:11]=[C:10]([O:15][CH3:16])[C:9]=1[O:17][CH3:18]

Participants

7

Reactant 4

HCID 112011,1-DibromoethaneHCID 2569301-Bromo-2,3,4-trimethoxybenzeneHCID 5462224MagnesiumHCID 86744366Bromide tetrahydrofuran

Product 1

HCID 178492974HCID 178492974, compound

Reagents, catalysts & solvents 2

HCID 193501Copper;dilithium;tetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (0.82 g, 33.74 mmol) was taken in flame dried 100 ml two necked flask and dry TEF (20 ml) was added. Then the dibromo ethane (0.1 ml) and trimethoxy bromobenzene (0.3 g, 1.20 mmol) were added at room temperature and stirred for 20 mins. The reaction initiates as indicated by temperature rise. The remaining bromide/THF (8.8 g, 35.48 mmol) in THF (20 ml) was added over 15 mints. After the addition was completed reaction mixture was stirred at 25° C. under nitrogen for 18 h. To the Grignard reagent at 0° C. was added a solution of dilithium tetrachlorocuprate (0.5 M, 0.76 ml, 0.38 mmol). The reaction was stirred at 0° C. for 15 mints and was used immediately for the coupling reaction.

Workup

  1. temperaturein flame
  2. dry with materialdried 100 ml two necked flask
  3. customdry TEF (20 ml)
  4. additionwas added
  5. additionAfter the addition
  6. customreaction mixture
  7. stirringwas stirred at 25° C. under nitrogen for 18 h
  8. stirringThe reaction was stirred at 0° C. for 15 mints
  9. customwas used immediately for the coupling reaction

Sources & evidence

ORD record
ord-912c8d44997d4e46b16e06fbb582f44f
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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