Reaction #2358523

Reaction equation

3-fluoro-5-methylsulfonyl-phenol

1.2-dibromoethane

potassium carbonate

→

title compound

Yield 73.0%

1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene

Yield 73.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe reaction mixtures
2. 2
   Temperaturewere cooled to room temperature
3. 3
   Filtrationfiltrated
4. 4
   OtherThe volatiles were evaporated
5. 5
   workup.ADDITIONaqueous sodium carbonate (100 ml, 10%) was added
6. 6
   Extractionthe mixture was extracted with ethyl acetate (2×100 ml)
7. 7
   WashThe combined organic phase was washed with brine (75 ml)
8. 8
   Dryingdried (Na2SO4)
9. 9
   Otherevaporated
10. 10
    OtherPurification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0)

Procedure

A mixture of 3-fluoro-5-methylsulfonyl-phenol (4.2 g, 22.08 mmol), 1.2-dibromoethane (24 ml, 27.7 mmol) and potassium carbonate (6.1 g, 44.2 mmol) in acetonitrile (36 ml) was divided into 6 aliquots which were each heated under microwave radiation at 120° C. for 30 min. The reaction mixtures were cooled to room temperature, filtrated and pooled. The volatiles were evaporated, aqueous sodium carbonate (100 ml, 10%) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with brine (75 ml), dried (Na2SO4) and evaporated. Purification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0) gave the title compound (4.77 g, 73%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Source