Triphenylphosphine → 1-Iodo-3-(3-phenylpropoxy)benzene

HRID 2095336Notes

Reaction equation

HRID 2095336 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:11][C:12]1[CH:13]=[C:14](O)[CH:15]=[CH:16][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[I:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([O:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 122723-IodophenolHCID 31234BenzenepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 593716201-Iodo-3-(3-phenylpropoxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round-bottom flask was placed 3-phenyl-1-propanol (2.00 g, 14.7 mmol, 1.5 equiv.), 3-iodophenol (2.16 g, 9.82 mmol) , triphenylphosphine (3.85 g, 14.7 mmol, 1.5 equiv.) and THF (40 mL). The mixture was stirred in a small ice bath. Neat diethyl azodicarboxylate (2.30 mL, 14.6 mmol, 1.5 equiv.) was added over a period of 30 min. The mixture was stirred in the ice bath for 20 h, then the bath was removed, and stirring was continued for 24 h at room temperature. The resulting mixture was concentrated under vacuum and diluted with EtOAc (200 mL). The solution was washed with brine (60 mL) and dried over Na2SO4. After evaporation, the residue was chromatographed on silica gel with EtOAc/petroleum ether 1:50. This resulted in 3.30 g (99%) of 1-iodo-3-(3-phenylpropoxy)benzene as light-yellow oil. 1H NMR (CDCl3, TMS, 300 MHz) δ 7.34-7.25 (m, 7H), 6.98 (t, 1H, J=8.0 Hz), 6.84 (dd, 1H, J=2.0, 8.2 Hz), 3.92 (t, 2H, J=6.5 Hz), 2.79 (t, 2H, J=7.7 Hz), 2.08 (m, 2H).

Workup

  1. customIn a 100 mL round-bottom flask was placed
  2. customthe bath was removed
  3. stirringstirring
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. additiondiluted with EtOAc (200 mL)
  6. washThe solution was washed with brine (60 mL)
  7. dry with materialdried over Na2SO4
  8. customAfter evaporation
  9. customthe residue was chromatographed on silica gel with EtOAc/petroleum ether 1:50
  10. customThis resulted in 3.30 g (99%) of 1-iodo-3-(3-phenylpropoxy)benzene as light-yellow oil

Sources & evidence

ORD record
ord-2e5da0c3795f493c8d90134c37c02de8
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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