Triphenylphosphine → 1-(3-Bromopropyl)-3-fluorobenzene

HRID 1093349Notes

Reaction equation

HRID 1093349 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:31]N1C(=O)CCC1=O>C(Cl)Cl>[Br:31][CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 149434163-(3-Fluorophenyl)propan-1-ol

Product 1

HCID 149434171-(3-Bromopropyl)-3-fluorobenzeneYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 23-1 (10.0 g) was dissolved in methylene chloride (100 ml), triphenylphosphine (17.5 g) and N-bromosuccinimide (11.8 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 3.5 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 alone) to give the object product (11.1 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 3.5 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 alone)

Sources & evidence

ORD record
ord-7826116563c6408f8ce9f04c9a05e7b3
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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