Triphenylphosphine → 1-(3-Bromopropyl)-2,4-dimethoxybenzene

HRID 1093341Notes

Reaction equation

HRID 1093341 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:13][CH2:12][CH2:11][C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 13758730HCID 13758730, compound

Product 1

HCID 283505521-(3-Bromopropyl)-2,4-dimethoxybenzeneYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 19-1 (2.68 g) was dissolved in methylene chloride (30 ml), triphenylphosphine (3.99 g) and N-bromosuccinimide (2.69 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give the object product (2.71 g) as a pale-brown oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. washThe reaction mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiethyl ether (100 ml) was added
  7. filtrationthe precipitated triphenylphosphine oxide was filtered off
  8. concentrationThe concentrate of the filtrate
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-d1a06a9850124fdabfeaf264b640473a
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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