Triphenylphosphine → 1-(3-Bromopropyl)naphthalene

HRID 1093464Notes

Reaction equation

HRID 1093464 reaction equation
[C:1]1([CH2:11][CH2:12][CH2:13]O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.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:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 147115183-(Naphthalen-1-yl)propan-1-ol

Product 1

HCID 147115191-(3-Bromopropyl)naphthaleneYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 73-1 (4.70 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (7.13 g) and N-bromosuccinimide (4.84 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr, and further at room temperature for 15 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 to give the object product (5.67 g) as a colorless 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

Sources & evidence

ORD record
ord-762941dcbcd7428ea34b89cca6e9862b
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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