Water → HCID 20553848, compound

HRID 1840234Notes

Reaction equation

HRID 1840234 reaction equation
[CH2:1]([OH:6])[C:2]([Br:5])([Br:4])[Br:3].C(N(CC)CC)C.[C:14](Cl)(=[O:17])[CH:15]=[CH2:16].O>C(OCC)C>[Br:3][C:2]([Br:5])([Br:4])[CH2:1][O:6][C:14](=[O:17])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6400TribromoethanolHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 20553848HCID 20553848, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A first solution including tribromoethanol (50 g, 177 mmol) and triethylamine (19.73 g, 195 mmol) dissolved in 50 g of diethylether was prepared. A second solution comprising acryloyl chloride (17.65 g, 195 mmol) dissolved in 50 g of diethylether was added dropwise to the first solution followed by stirring for four hours at room temperature. The resulting solution was then added to water, and the organic phase was extracted. The organic phase was distilled to yield 48.38 g of TBEA (72.5% yield).

Workup

  1. customwas prepared
  2. additionwas added dropwise to the first solution
  3. extractionthe organic phase was extracted
  4. distillationThe organic phase was distilled
  5. customto yield 48.38 g of TBEA (72.5% yield)

Sources & evidence

ORD record
ord-f4f938c10b6e48868ff1cbb3d762d1f9
Source dataset
uspto-grants-2004_01
Patent number
US06680160B2

Reaction notes

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