1-Bromo-2-(chloromethoxy)ethane → 2-(2-Bromoethoxy)-1,1,1-trinitroethane

HRID 1252750Notes

Reaction equation

HRID 1252750 reaction equation
[Br:1][CH2:2][CH2:3][O:4][CH2:5]Cl.[CH:7]([N+:14]([O-:16])=[O:15])([N+:11]([O-:13])=[O:12])[N+:8]([O-:10])=[O:9].[K]>>[Br:1][CH2:2][CH2:3][O:4][CH2:5][C:7]([N+:14]([O-:16])=[O:15])([N+:11]([O-:13])=[O:12])[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 51228801-Bromo-2-(chloromethoxy)ethane2×HCID 86742175CID 86742175

Product 1

HCID 138979682-(2-Bromoethoxy)-1,1,1-trinitroethane

Procedure

2,2,2-trinitroethyl 2-nitroxyethyl ether (TNEN) is prepared by the reaction of potassium nitroform with chloromethyl 2 2-bromoethyl ether to form 2,2,2-trinitroethyl 2-bromoethyl ether which is then reacted with silver nitrate to form the desired product TNEN as shown in the following reaction scheme: ##STR1## Example 1 shows a method of preparing the starting material chloromethyl 2-bromoethyl ether. Example 2 illustrates suitable conditions for reacting potassium nitroform with chloromethyl 2-bromoethyl ether to produce the intermediate product 2,2,2-trinitroethyl 2-bromoethyl ether. Finally, example 3 illustrates suitable conditions for reacting the 2,2,2-trinitroethyl 2-bromoethyl ether with silver nitrate to produce the final product 2,2,2-trinitroethyl 2-nitroxyethyl ether.

Workup

  1. customas shown in the following reaction scheme

Sources & evidence

ORD record
ord-9264dcdfca3a4a4a96618eefc1806d53
Source dataset
uspto-grants-1988_05
Patent number
US04745208

Reaction notes

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