1,2-Dibromoethane → HCID 18362251, compound

HRID 382908Notes

Reaction equation

HRID 382908 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH3:3].[Br:12][CH2:13][CH2:14]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide2×HCID 111162393-propoxyphenol

Product 1

HCID 18362251HCID 18362251, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×

Procedure

A solution of 3-(n-propoxy)phenol (15.2 g; 0.1 mol; from Example A above) in 1,2-dibromoethane (100 ml; 1.16 mol) was added to a solution of tetrabutylammonium hydrogen sulphate (34 g; 0.1 mol) and sodium hydroxide (8.0 g; 0.2 mol) in water (100 ml). The mixture was stirred vigorously whilst a 50% solution of sodium hydroxide in water (33 ml) was added dropwise over half an hour. Stirring was subsequently continued for one hour. The organic phase was separated, washed with water and dried over magnesium sulphate. The solvent was evaporated and the residue treated with diethyl ether (150 ml). The precipitated salt was removed by filtration and the diethyl ether evaporated. The residue was distilled to yield (14.0 g; 54%) of the title compound as an oil (97% purity). bp 112-115° C. (0.05 mm Hg) MW=259 (GC-MS)

Workup

  1. additionwas added dropwise over half an hour
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated
  6. additionthe residue treated with diethyl ether (150 ml)
  7. customThe precipitated salt was removed by filtration
  8. customthe diethyl ether evaporated
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b4e2c18fbc384a2994ade43314599ec0
Source dataset
uspto-grants-2001_10
Patent number
US06310252B1

Reaction notes

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