1,2-Dibromoethane → HCID 66597559, compound

HRID 630379Notes

Reaction equation

HRID 630379 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Br:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:11][CH2:12][CH2:13][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 66597559HCID 66597559, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-hydroxyethyl)phenol (5 g, 0.035 mol) in acetone (50 mL) was added 1,2-dibromoethane (15.6 mL, 1.3 mol) and potassium carbonate (13 g, 0.09 mol). The mixture was stirred at 80° C. for 48 hours. The salts were filtered and the mixture was evaporated. The crude obtained was partitioned between ethyl acetate/water. The organic layer was washed with sodium hydroxide 2N, water and brine, dried, filtered and the solvent was removed under reduced pressure to give the title compound as a white solid (73%), which was used in the next step without further purification.

Workup

  1. filtrationThe salts were filtered
  2. customthe mixture was evaporated
  3. customThe crude obtained
  4. customwas partitioned between ethyl acetate/water
  5. washThe organic layer was washed with sodium hydroxide 2N, water and brine
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-819145c621624bbf8673df169549c38a
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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