1,2-Dibromoethane → HCID 14879552, compound

HRID 1975697Notes

Reaction equation

HRID 1975697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.Cl.[NH2:13][OH:14].C[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[O:11][CH2:26][CH2:25][O:14][N:13]=1

Participants

11

Reactant 5

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 17124o-Chlorophenylacetic acidHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 14879552HCID 14879552, compound

Reagents, catalysts & solvents 5

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 5.0 g (29.3 mmole) of o-chlorophenylacetic acid and 0.3 g of p-toluenesulfonic acid monohydrate in 50 ml of methanol was heated under reflux for 6 hours. At the end of this time, 3.1 g (44 mmole) of hydroxylamine hydrochloride were added to the reaction mixture, followed by 2.1 g of sodium methoxide. The resulting reaction mixture was then heated under reflux for 10 hours. 14.2 g (103 mmole) of potassium carbonate and 5.1 ml of 1,2-dibromoethane were then added to the resulting reaction mixture, followed by 15 ml of water. The reaction mixture was then heated under reflux for a further 10 hours. At the end of this time, 200 ml of ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 4.9 g of the title compound as an oil.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe resulting reaction mixture
  3. temperaturewas then heated
  4. temperatureunder reflux for 10 hours
  5. temperatureThe reaction mixture was then heated
  6. temperatureunder reflux for a further 10 hours
  7. customthe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was then removed by distillation under reduced pressure
  11. customThe residue thus obtained

Sources & evidence

ORD record
ord-eed5e7d591af4187be068bf1aabe7b4d
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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