Triphenylphosphine → HCID 20231593, compound

HRID 2290609Notes

Reaction equation

HRID 2290609 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Br:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1([P:18](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[Br-:9].[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][PH3+:18])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 20231593HCID 20231593, compoundYield 161.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Nitrobenzylbromide (54.0 g, 0.25 mol) and triphenylphosphine (65.6 g, 0.25 mol) were dissolved in 150 mL of dry benzene in a flask equipped with a drying tube. The solution was heated on a steam bath with swirling until a majority of product had precipitated (5 min), and then was allowed to cool to near ambient temperature with occasional agitation. Filtration of the precipitate and washing with 3×200 mL anhydrous ether yielded 100.8 g of the desired product as an off-white powder. The filtrate was flash evaporated to 50 mL and heated on a steam bath for 5 min, then chilled overnight to provide an additional 11.4 g of product (93.8% yield).

Workup

  1. customequipped with a drying tube
  2. temperatureThe solution was heated on a steam bath
  3. customhad precipitated (5 min)
  4. filtrationFiltration of the precipitate
  5. washwashing with 3×200 mL anhydrous ether

Sources & evidence

ORD record
ord-d4f55246d72b48a4808c390ca889cd9e
Source dataset
uspto-grants-1986_10
Patent number
US04617398

Reaction notes

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