Compounds derived from halogenoacetic acids
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C8H5BrI2O2 Synthesis
OH I
mol.wt. 466.84
COCH2Br
I
-Preparation by bromination of 2-hydroxy-3,5-diiodoacetophenone in acetic acid at 70-80°, under light irradiation (84%) [332]. m.p. 150-151° [332].
2-Bromo-1-(4-hydroxy-3,5-diiodophenyl)ethanone [31827-97-1]
C8H5BrI2O2 Synthesis
OH I
mol.wt. 466.84
I
-Preparation by reaction of bromine on 4-hydroxy-3,5-diiodoacetophenone in boiling chloroform under light irradiation (81-83%) [330] [331].
COCH2Br
m.p. 171-172° [330] [331]; UV [330].
2-Bromo-1-(4-hydroxy-3,5-dinitrophenyl)ethanone [120388-18-3]
C8H5BrN2O6 Synthesis
OH NO2
mol.wt. 305.04
NO2
COCH2Br
-Preparation by bromination of 4-hydroxy-3,5-dinitroacetophenone with cupric bromide in refluxing ethyl acetate (60%) [210]. m.p. 92-94° [210]; Crystal Data [210].
2-Bromo-1-(3,5-dibromo-2-hydroxyphenyl)ethanone [194226-52-3]
C8H5Br3O2 Syntheses
OH Br
COCH2Br
Br
mol.wt. 372.84
-Preparation by action of bromine with 3,5-dibromo-2-hydroxyacetophenone in refluxing acetic acid for 2.5 h (55%) [490]. -Also obtained by reaction of bromine with 2-hydroxyacetophenone in chloroform in an ice bath for 2 h [1308]. m.p. 107-108° [490];
1H
NMR [490], IR [490].
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HYDROXYACETOPHENONES
2-Bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanone [34969-79-4]
C8H5Br3O2 Synthesis
OH Br
mol.wt. 372.84
Br
-Preparation by bromination of 3,5-dibromo-4-hydroxyacetophenone in chloroform [1108] [1201] [1246], (79%) [1246].
COCH2Br
m.p. 137° [1246], 128° [1108] [1201].
2-Bromo-1-(3,5-dibromo-2,4-dihydroxyphenyl)ethanone C8H5Br3O3 Synthesis
OH Br
mol.wt. 388.84
Br
-Preparation by bromination of resacetophenone in acetic acid [1303].
OH COCH2Br
m.p. 112-113° [1303].
2-Bromo-1-(3,5-dibromo-2,6-dihydroxyphenyl)ethanone [74815-26-2]
C8H5Br3O3 Synthesis
OH Br
mol.wt. 388.84
COCH2Br
-Preparation by bromination of 2,6-dihydroxyacetophenone with cupric bromide in refluxing chloroform-ethyl acetate mixture [109].
OH Br
m.p. 150° [109].
2-Bromo-1-(3-chloro-4-hydroxyphenyl)ethanone [41877-19-4]
C8H6BrClO2
mol.wt. 249.49
Syntheses
OH Cl
-Preparation by selective bromination of 3-chloro-4-hydroxyacetophenone with dioxane dibromide in dioxane-ethyl ether mixture at r.t. (85%) [1150]. -Preparation by selective bromination of 3-chloro-4-hydroxyacetophenone with cupric bromide in refluxing chloroformethyl acetate mixture [807], (100%) [1340].
COCH2Br m.p. 128-130° [1150];
1H
NMR [1150].
COMPOUNDS DERIVED FROM HALOGENOACETIC ACIDS 2-Bromo-1-(4-chloro-2-hydroxyphenyl)ethanone [157068-00-3]
C8H6BrClO2
mol.wt. 249.49
Synthesis
OH COCH2Br Cl
-Obtained by reaction of bromoacetyl bromide on 3-chloroanisole with aluminium chloride in carbon tetrachloride, first at 0°, then at r.t. (16%) [35].
2-Bromo-1-(4-chloro-3-hydroxyphenyl)ethanone [73898-34-7]
C8H6BrClO2
mol.wt. 249.49
Synthesis
OH Cl COCH2Br
-Preparation by reaction of dioxane dibromide on 4-chloro-3-hydroxyacetophenone in dioxane-ethyl ether mixture at r.t. (84%) [888].
2-Bromo-1-(5-chloro-2-hydroxyphenyl)ethanone [52727-99-8]
C8H6BrClO2
mol.wt. 249.
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