Carbon tetrabromide → 4-(2,2-Dibromovinyl)-2-fluoro-1-methoxybenzene

HRID 1400606Notes

Reaction equation

HRID 1400606 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[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:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 676963-Fluoro-p-anisaldehyde

Product 1

HCID 594550774-(2,2-Dibromovinyl)-2-fluoro-1-methoxybenzeneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluoro-4-methoxy benzaldehyde (0.5 g, 0.00324 mol) was dissolved in DCM (30 mL). Carbon tetrabromide (2.15 g, 0.0064 mol) and triphenylphosphine (3.4 g, 0.013 mol) were added to the solution followed by stirring at RT for 3 h. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh) to provide the desired compound as a yellow colored oil (0.6 g, 60% yield).

Workup

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh)

Sources & evidence

ORD record
ord-5f0b8656fefb40e0939b107f79945d6f
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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