Triphenylphosphine → 4-(3-Bromopropyl)-2-methoxy-1-methylbenzene

HRID 368337Notes

Reaction equation

HRID 368337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12]O)[CH:6]=[CH:7][C:8]=1[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]N1C(=O)CCC1=O>C(Cl)Cl>[Br:33][CH2:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 10997638Npc191948

Product 1

HCID 186265044-(3-Bromopropyl)-2-methoxy-1-methylbenzeneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, a solution of 7.33 g (40.7 mmol) of 3-(3-methoxy-4-methylphenyl)-1-propanol in 200 mL of CH2Cl2 was treated with 10.67 g (40.7 mmol) of triphenylphosphine followed in portions by 7.3 g (40.7 mmol) of recrystallized N-bromosuccinimide. The solution was stirred at room temperature for 2 hours, then filtered through flash silica gel. Removal of the solvent under reduced pressure left 8.68 g (87.9% yield) of the product as a clear oil. The structure was confirmed by NMR spectroscopy.

Workup

  1. filtrationfiltered through flash silica gel
  2. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-94a669e158a24e9895f00674a10b5446
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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