N-bromobutanimide → Di(tert-butyl) [4-(bromomethyl)benzoyl]phosphonate

HRID 566492Notes

Reaction equation

HRID 566492 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([P:8](=[O:19])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7])=[CH:4][CH:3]=1.C1C(=O)N([Br:29])C(=O)C1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl.CCCCCC.CCOC(C)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:29][CH2:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([P:8](=[O:19])([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 54190661Di(tert-butyl) (4-methylbenzoyl)phosphonate

Product 1

HCID 54361205Di(tert-butyl) [4-(bromomethyl)benzoyl]phosphonateYield 22.4%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of di(tert-butyl) (4-methylbenzoyl)phosphonate (10 g), NBS (8.3 g), NaHCO3 (10 g) and benzoyl peroxide (0.1 g) in 200 mL of CCl4 was heated to reflux for 20 min. The mixture was cooled to room temperature, diluted with 200 mL of 10:1 hexane/EtOAc and filtered through a pad of silca gel. The filtrate was concentrated and the residue was swished from hexane to give 2.8 g of the title compound as a beige solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 min
  3. filtrationfiltered through a pad of silca gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7329bc2c793c4ba3805ddb4ef22271bc
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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