Benzoyl bromide → 1-Methylbut-1-en-3-onyltin bromide dichloride

HRID 399290Notes

Reaction equation

HRID 399290 reaction equation
[Sn:1]([Cl:3])[Cl:2].[C:4]([CH2:7][C:8](=[O:10])[CH3:9])(=O)[CH3:5].C([Br:19])(=O)C1C=CC=CC=1>C(OCC)C>[CH3:5][C:4]([Sn:1]([Br:19])([Cl:3])[Cl:2])=[CH:7][C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 12056Benzoyl bromideHCID 24479Stannous ChlorideHCID 31261Acetylacetone

Product 1

HCID 857666391-Methylbut-1-en-3-onyltin bromide dichlorideYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

39.8 g (0.21 mol) of tin(II) chloride and 21.0 g (0.21 mol) of acetylacetone in 200 ml of diethyl ether were placed in a reactor. 38.8 g (0.21 mol) of benzoyl bromide were metered in over 15 min at room temperature, with stirring, a rise in temperature to the reflux point being recorded. After a postreaction time of 1 h at the reflux temperature, the mixture was cooled and the crystalline precipitate was separated off. 48 g (65% of theory) of 1-methylbut-1-en-3-onyltin bromide dichloride (BrCl2Sn--C(CH3)=CH--CO--CH3) were isolated.

Workup

  1. customwere metered in over 15 min at room temperature
  2. temperatureAfter a postreaction time of 1 h at the reflux temperature, the mixture was cooled
  3. customthe crystalline precipitate was separated off

Sources & evidence

ORD record
ord-74cd980bc0894e0cb08fba6a83e17bf6
Source dataset
uspto-grants-1998_10
Patent number
US05817851

Reaction notes

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