Triphenylphosphine → 1-Bromo-4-phenylbutane

HRID 1743445Notes

Reaction equation

HRID 1743445 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][Br:38])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 76889Benzenebutanol

Product 1

HCID 2596681-Bromo-4-phenylbutaneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenyl-1-butanol (5.00 g, 33.3 mmol) and CH2Cl2 (250 mL) at 0° C. was added triphenylphosphine (13.1 g, 50.0 mmol) followed by NBS (8.90 g, 50.0 mmol). After stirring at this temperature for 2 h, the mixture was quenched with H2O (50 mL) and extracted with CH2Cl2 (150 mL) The organic layer was washed with brine (40 mL) and dried (Na2SO4). After concentration, the residue was flushed through two quick columns of silica gel using 2% EtOAc/petroleum ether as an eluant to afford 4-phenylbutyl bromide (6.22 g, 88%) as an intermediate.

Workup

  1. customthe mixture was quenched with H2O (50 mL)
  2. extractionextracted with CH2Cl2 (150 mL) The organic layer
  3. washwas washed with brine (40 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was flushed through two quick columns of silica gel using 2% EtOAc/petroleum ether as an eluant

Sources & evidence

ORD record
ord-be264e8f63f34efdac26365abe779a16
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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