Pentane → HCID 19422270, compound

HRID 744701Notes

Reaction equation

HRID 744701 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O.CCCCC>C(Cl)Cl.[Zn]>[Br:2][C:1]([Br:5])=[CH:34][C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 190687272-[(Pyridin-2-yl)oxy]benzaldehyde

Product 1

HCID 19422270HCID 19422270, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of carbon tetrabromide (54.09 g, 162.9 mmol), and zinc (10.97 g, 162.9 mmol) in CH2Cl2 (800 mls) was added triphenylphosphine (42.68 g, 162.9 mmol) and the mixture was allowed to stir for 18 hrs. 2-(2-Pyridyloxy)benzaldehyde (16.21 g, 81.5 mmol) was then added as a solution in CH2Cl2 (50 mls) and the reaction was stirred for 2 hrs. It was then poured into pentane (1.6 liters) with good stirring, then allowed to stand for 1 hr. The solution was decanted and concentrated. The residue left after decantation was taken up in 1N NaOH (500 mls) and filtered through Celite. It was then washed with CH2Cl2 (500 mls). This organic was dried with MgSO4, concentrated and combined with the material obtained from the decanted solution to afford 29.01 g of 1,1-dibromo-2-(2-(2-pyridyloxy)phenyl)ethene as an off-white solid.

Workup

  1. stirringthe reaction was stirred for 2 hrs
  2. waitto stand for 1 hr
  3. customThe solution was decanted
  4. concentrationconcentrated
  5. waitThe residue left after decantation
  6. filtrationfiltered through Celite
  7. washIt was then washed with CH2Cl2 (500 mls)
  8. dry with materialThis organic was dried with MgSO4
  9. concentrationconcentrated
  10. customobtained from the decanted solution

Sources & evidence

ORD record
ord-7bc1e07b7149447d9299af5acdb9165f
Source dataset
uspto-grants-1996_09
Patent number
US05559144

Reaction notes

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