Carbon tetrabromide → HCID 59455124, compound

HRID 1401674Notes

Reaction equation

HRID 1401674 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][N:5]=1)[CH2:2][CH3:3].[C:12](Br)(Br)([Br:14])[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:13][C:12]([Br:14])=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([CH2:1][CH2:2][CH3:3])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 450798906-Propylpyridine-3-carbaldehyde

Product 1

HCID 59455124HCID 59455124, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Propylnicotinaldehyde (0.2 g, 0.00134 mol) was dissolved in DCM (4 mL). Carbon tetrabromide (0.887 g, 0.00268 mol) and triphenylphosphine (1.4 g, 0.00536 mol) were added to the solution followed by stirring at RT overnight. After insoluble matter was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography (3% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (0.05 g).

Workup

  1. customAfter insoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through column chromatography (3% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-1c5754b1a52145e3861e6be6f99725ca
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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