1,2-Dibromoethane → HCID 22470635, compound

HRID 394980Notes

Reaction equation

HRID 394980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:10][CH2:11][CH2:12][O:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 943922,6-Difluorophenol

Product 1

HCID 22470635HCID 22470635, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 10 g of 2,6-difluorophenol, 40.5 cm3 of 1,2-dibromoethane and 15.3 g of potassium carbonate in 300 cm3 of acetonitrile was heated for 18 hours at a temperature in the region of 75° C., with stirring and under an inert atmosphere. After cooling to a temperature in the region of 20° C., the reaction mixture was filtered and washed with 3 times 30 cm3 of acetonitrile. The filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was taken up in 200 cm3 of petroleum ether (40-65° C.), filtered and washed with 3 times 30 cm3 of petroleum ether (40-65° C.). The filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45μ; diameter 7 cm; height: 28 cm), eluting with petroleum ether (40-65° C.) and collecting 100-cm3 fractions. Fractions 22 to 58 were combined and then concentrated to dryness under the above conditions. 14.5 g of 1-(2-bromoethoxy)-2,6-difluorobenzene were obtained in the form of a thick colorless oil.

Workup

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe reaction mixture was filtered
  3. washwashed with 3 times 30 cm3 of acetonitrile
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  5. customThe residue obtained
  6. filtrationfiltered
  7. washwashed with 3 times 30 cm3 of petroleum ether (40-65° C.)
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  9. customThe residue obtained
  10. customwas purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45μ; diameter 7 cm; height: 28 cm)
  11. washeluting with petroleum ether (40-65° C.)
  12. customcollecting 100-cm3 fractions
  13. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-6531b058c452479c9ccaa11cb284d986
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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