Sodium hydride → 2-[2-(4-Bromo-3,5-dichlorophenoxy)ethoxy]naphthalene
Reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[Cl:10].[H-].[Na+].CS(O[CH2:18][CH2:19][O:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)(=O)=O>CN(C)C=O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH2:18][CH2:19][O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)=[CH:4][C:3]=1[Cl:10]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
A stirred mixture of 4-bromo-3,5-dichlorophenol (1.9 g) in dimethylformamide (20 mL) under argon was treated with 55% sodium hydride (0.345 g), stirred for 30 minutes and treated with 2-(2-naphthalenyloxy)ethyl methanesulfonate (2.1 g). The mixture was heated at 60° C. overnight and evaporated to dryness. The residue was mixed with water and excess sodium hydroxide solution, the product was extracted twice with dichloromethane, and the organic layers were washed with water. The combined organic layers were dried (Na2SO4), filtered, evaporated and crystallized from dichloromethane-diethyl ether to provide 3.3 g of 2-[2-(4-bromo-3,5-dichlorophenoxy)ethoxy]naphthalene as a colorless solid, mp 140°-142° C.
Workup
- customevaporated to dryness
- additionThe residue was mixed with water and excess sodium hydroxide solution
- extractionthe product was extracted twice with dichloromethane
- washthe organic layers were washed with water
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customcrystallized from dichloromethane-diethyl ether
Sources & evidence
- ORD record
- ord-ef7969e5be234a7183248b22bd9486c4
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
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