Water → 3-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

HRID 1612033Notes

Reaction equation

HRID 1612033 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26]Cl.O>CN(C=O)C>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 46704942-(1-Adamantyl)-4-bromophenol

Product 1

HCID 153780873-(1-Adamantyl)-1-bromo-4-methoxyethoxymethoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3.8 g (0.13 mol) of sodium hydride (80% in oil) and 50 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. A solution of 40.0 g (0.13 mol) of 2-(1-adamantyl)-4-bromophenol dissolved in 100 ml of DMF was added dropwise and the mixture was stirred until the evolution of gas had ceased. A solution of 18 ml (0.15 mol) of 2-methoxy-ethoxymethyl chloride in 20 ml of DMF was then added dropwise and the mixture was stirred for four hours at room temperature. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a column of silica eluted with a mixture of dichloromethane and hexane (50/50). After evaporation of the solvents, 40.1 g (78%) of the expected product, with a melting point of 69–70° C., was collected.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred for four hours at room temperature
  3. extractionextracted with ethyl ether
  4. customThe organic phase was separated out
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by chromatography on a column of silica
  9. washeluted with a mixture of dichloromethane and hexane (50/50)
  10. customAfter evaporation of the solvents, 40.1 g (78%) of the expected product
  11. customwith a melting point of 69–70° C., was collected

Sources & evidence

ORD record
ord-ecfdec41ab4941ad92062635a1ee3e32
Source dataset
uspto-grants-2006_01
Patent number
US06992095B2

Reaction notes

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