1,2-Dibromoethane → HCID 22471323, compound

HRID 394998Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[Br:16][CH2:17][CH2:18]Br>C(#N)C>[Br:16][CH2:17][CH2:18][O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 15 g of 3,4-difluorophenol, 23.5 g of potassium carbonate and 60 cm3 of 1,2-dibromoethane in 250 cm3 of acetonitrile was stirred at a temperature in the region of 70° C. for 18 hours. After cooling to about 20° C., the reaction mixture was filtered through Celite and then 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 70-200μ; diameter 8 cm; mass 400 g), eluting with 40-60° C. petroleum ether. The fractions containing the product were combined and then concentrated to dryness under reduced pressure (2 kPa) in the region of 40° C. 15.7 g of 4-(2-bromoethoxy)-1,2-difluorobenzene were obtained in the form of an oil.

Workup

temperatureAfter cooling to about 20° C.
filtrationthe reaction mixture was filtered through Celite
concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
customThe residue obtained
customwas purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 70-200μ; diameter 8 cm; mass 400 g)
washeluting with 40-60° C. petroleum ether
additionThe fractions containing the product
concentrationconcentrated to dryness under reduced pressure (2 kPa) in the region of 40° C

Sources & evidence

ORD record: ord-bd1af2eef62c44f3a6468a8a9e3c366b
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603005B2

Reaction notes

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