تفاعل #69548

معادلة التفاعل

1-[2,6-dimethoxy-4-(methoxymethyl)phenyl]ethanone

triethylamine

tert-butyldimethylsilyl trifluoromethanesulfonate

ammonium chloride

N-bromosuccinimide

tetrabutylammonium fluoride

sodium hydrogencarbonate

→

title compound

المردود 88.2%

2-Bromo-[2,6-dimethoxy-4-(methoxymethyl)phenyl]ethanone

المردود 88.2%

المذيبات

tetrahydrofuran

n-heptane ethyl acetate

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   درجة الحرارةwhile cooling on ice
3. 3
   workup.STIRRINGthe mixture was stirred for 1.5 hours
4. 4
   استخلاصthe reaction mixture was extracted with ethyl acetate
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   درجة الحرارةwhile cooling on ice
8. 8
   workup.STIRRINGthe mixture was stirred for 30 minutes
9. 9
   استخلاصthe mixture was extracted with ethyl acetate
10. 10
    تجفيفdried over magnesium sulfate
11. 11
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
12. 12
    أخرىThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

الإجراء التجريبي

To a tetrahydrofuran (120 mL) solution of 1-[2,6-dimethoxy-4-(methoxymethyl)phenyl]ethanone (10.0 g, 44.9 mmol) was added triethylamine (18.8 ml, 135 mmol), and tert-butyldimethylsilyl trifluoromethanesulfonate (15.5 ml, 67.4 mmol) was added dropwise while cooling on ice, and the mixture was stirred for 30 minutes. N-bromosuccinimide (12.0 g, 67.4 mmol) was added and the mixture was stirred for 1.5 hours. To the reaction mixture, a saturated aqueous solution sodium hydrogencarbonate was added, and the reaction mixture was extracted with ethyl acetate, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. To a tetrahydrofuran (80 mL) solution was added dropwise tetrabutylammonium fluoride (1M, 40.4 ml, 40.4 mmol) while cooling on ice, and the mixture was stirred for 30 minutes. To the mixture was added a saturated aqueous solution of ammonium chloride and the mixture was extracted with ethyl acetate and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate 3/1 then 2/1) to obtain the title compound (12.0 g, 39.6 mmol).

المصدر