1,2-Dibromoethane → 124438-12-6

HRID 484475Notes

Reaction equation

HRID 484475 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12].[Br:13][CH2:14][CH2:15]Br>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Br:13][CH2:14][CH2:15][O:12][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[Cl:3]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 874592-Chloro-4-methoxyphenol

Product 1

HCID 14989173124438-12-6Yield 52.7%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

To a stirred mixture of 0.5 parts of N,N,N-triethylbenzenemethanaminium chloride, 4 parts to sodium hydroxide and 40 parts of water were added dropwise 16 parts of 2-chloro-4-methoxyphenol and 18.2 parts of 1,2-dibromoethane at 50° C. Upon complete addition, stirring was continued overnight at 50° C. The reaction mixture was poured into water and the product was extracted with a mixture of 2,2'-oxybispropane and dichloromethane. The extract was dried, filtered and evaporated, yielding 14 parts (52.7%) of 1-(2-bromoethoxy)-2-chloro-4-methoxybenzene as a residue (int. 5).

Workup

  1. additionUpon complete addition
  2. extractionthe product was extracted with a mixture of 2,2'-oxybispropane and dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-620dd260c5ef4134bcf01950702c684f
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

Loading…