Triphenylphosphine → 1-(2-Bromoethyl)-4-methoxybenzene

HRID 1006889Notes

Reaction equation

HRID 1006889 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:31]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][Br:31])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 697054-Methoxyphenethyl alcohol

Product 1

HCID 844271-(2-Bromoethyl)-4-methoxybenzeneYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxyphenethyl alcohol (50 g) and triphenylphosphine (103 g) were dissolved in methylene chloride (600 ml), followed by the addition of N-bromosuccinimide (70 g) in small portions under ice-cooling, and the resulting mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated, and to the resulting residue was added hexane. The insoluble matters were filtered off, while the resulting filtrate was evaporated, to give the title compound as a colorless oil (50.32 g, yield; 71%).

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated
  3. additionto the resulting residue was added hexane
  4. filtrationThe insoluble matters were filtered off, while the resulting filtrate
  5. customwas evaporated

Sources & evidence

ORD record
ord-99f99fe7ad5e4042bf426509a87d034a
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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