Ethyl vinyl ether → 2-Bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one

HRID 2102871Notes

Reaction equation

HRID 2102871 reaction equation
[CH2:1]([O:3][CH:4]=[CH2:5])[CH3:2].[Br:6][CH:7]([CH3:17])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:9]>C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[Br:6][CH:7]([CH3:17])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:1]([O:3][CH2:4][CH3:5])[CH3:2])=[CH:12][CH:11]=1)=[O:9]

Participants

5

Reactant 2

HCID 8023Ethyl vinyl etherHCID 126131632-Bromo-1-(4-hydroxyphenyl)propan-1-one

Product 1

HCID 442497132-Bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-oneYield 103.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

Ethoxyethene (3.148 g, 43.655 mmol) and TFA (0.249 g, 2.183 mmol) was added to a suspension of 2-bromo-1-(4-hydroxyphenyl)propan-1-one (5.000 g, 21.827 mmol) in toluene (50 ml) at rt. The reaction mixture was stirred at 30° C. for 2 h and 30 min. The solvent was evaporated to yield the product as an oil (6.83 g, 100%).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-69b1d323028f4e8881675e80675bddb9
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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