Triphenylphosphine → Methyl 1-(4'-bromomethylphenyl)cyclopent-3-ene-1-carboxylate

HRID 1463529Notes

Reaction equation

HRID 1463529 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.O[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:35]([O:37][CH3:38])=[O:36])[CH2:34][CH:33]=[CH:32][CH2:31]2)=[CH:26][CH:25]=1>C(Cl)Cl>[Br:20][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:35]([O:37][CH3:38])=[O:36])[CH2:34][CH:33]=[CH:32][CH2:31]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 19090695Methyl 1-(4'-hydroxymethylphenyl)cyclopent-3-ene-1-carboxylate

Product 1

HCID 19090689Methyl 1-(4'-bromomethylphenyl)cyclopent-3-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (8.03 g, 30.6 mmol) in 100 ml CH2Cl2 at 0° C. was added dropwise bromine (1.45 ml, 28.1 mmol). After 15 minutes at 0° C. a white precipitate formed and a solution of the product of Step 3, above, (5.93 g, 25.5 mmol) in 30 ml CH2Cl2 was added dropwise. After 1 hour the solvent was removed in vacuo and the residue was taken up in ether to precipitate the triphenylphosphine oxide formed in the reaction. After filtration, evaporation and SGC (5% EtOAc-hexanes) the title compound (5 g) was obtained as a colorless oil which crystallized on standing.

Workup

  1. customAfter 15 minutes at 0° C. a white precipitate formed
  2. customAfter 1 hour the solvent was removed in vacuo
  3. customto precipitate the triphenylphosphine oxide
  4. customformed in the reaction
  5. filtrationAfter filtration, evaporation and SGC (5% EtOAc-hexanes) the title compound (5 g)
  6. customwas obtained as a colorless oil which
  7. customcrystallized

Sources & evidence

ORD record
ord-9249d368fe12463c874b9dcc8260c04b
Source dataset
uspto-grants-1994_04
Patent number
US05300668

Reaction notes

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