Hydrogen Bromide → 4H-1,3-Dioxin-4-one, 5-bromo-2,2,6-trimethyl-

HRID 1380638Notes

Reaction equation

HRID 1380638 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:12])[O:9][C:8](=[O:10])[CH:7]=[C:6]([CH3:11])[O:5]1.Br.CCOCC.CCCCCC>C(Cl)Cl>[Br:1][C:7]1[C:8](=[O:10])[O:9][C:4]([CH3:12])([CH3:3])[O:5][C:6]=1[CH3:11]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 21584099Diethylether hexane

Product 1

HCID 103534354H-1,3-Dioxin-4-one, 5-bromo-2,2,6-trimethyl-Yield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.105 mol, 5.38 ml) was added dropwise to a 20° C. solution of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TKD, 0.1 mol, 14.2 g) in 100 ml CH2Cl2 over five minutes. The reaction solution was rapidly decolorized and hydrogen bromide evolved. After 15 minutes, the solvent was removed in vacuo to provide 22 g (99%, >95% pure by NMR) of a pale yellow oil which solidified upon refrigeration. Flash chromatography (10% ether/hexane on silica) afforded 16.5 g (75%) of the title compound as colorless plates.

Workup

  1. customthe solvent was removed in vacuo
  2. customto provide 22 g (99%, >95% pure by NMR) of a pale yellow oil which

Sources & evidence

ORD record
ord-c39d5e366b2f440fac5b146d43dae0f8
Source dataset
uspto-grants-1986_04
Patent number
US04582913

Reaction notes

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