2-[2-(4-Bromophenyl)ethoxy]ethanol → HCID 13208939, compound

HRID 2078424Notes

Reaction equation

HRID 2078424 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1.[C:14]([Cu])#[N:15]>CN(C=O)C>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1)#[N:15]

Participants

4

Reactant 2

HCID 691375802-[2-(4-Bromophenyl)ethoxy]ethanolHCID 178418546HCID 178418546, compound

Product 1

HCID 13208939HCID 13208939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 2-[2-(4-bromophenyl)ethoxy]ethanol (10.8 g, 0.044 mol; see step (iii) above in DMF (100 mL), CuCN (7.8 g, 0.088 mol) was added and refluxed at 140 to 150° C. overnight. After removal of DMF by distillation, the reaction was quenched by the addition of water. Inorganic matter was removed by filtration and the aqueous layer was extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with water and brine before being concentrated. The crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether:ethyl acetate (75:25) eluent). This yielded 4.3 g (51%) of the sub-title compound.

Workup

  1. additionwas added
  2. customAfter removal of DMF
  3. distillationby distillation
  4. customthe reaction was quenched by the addition of water
  5. customInorganic matter was removed by filtration
  6. extractionthe aqueous layer was extracted with ethyl acetate (4×100 mL)
  7. washThe combined organic layers were washed with water and brine
  8. concentrationbefore being concentrated
  9. customThe crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether:ethyl acetate (75:25) eluent)

Sources & evidence

ORD record
ord-59c8650abae344b583af1331eaf069b7
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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