1,4-Dibromobutane → Diethyl (4-bromobutyl)phosphonate

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[CH2:7]([O:9][P:10]([O:14]CC)[O:11][CH2:12][CH3:13])[CH3:8]>>[CH2:7]([O:9][P:10]([CH2:5][CH2:4][CH2:3][CH2:2][Br:1])(=[O:14])[O:11][CH2:12][CH3:13])[CH3:8]

Participants

Reactant 2

HCID 80561,4-Dibromobutane

HCID 31215Triethyl phosphite

Product 1

HCID 14411016Diethyl (4-bromobutyl)phosphonate

Procedure

In another method, 1,4-dibromobutane is heated with triethylphosphite to give diethyl-4-bromobutylphosphonate, for example, as described by Eberhard and Westheimer, 1965. The resultant bromide is then reacted with, for example, biphenyl-4-carboxylic acid in dimethylformamide, in the presence of potassium carbonate. Again, the phosphate ester groups, e.g., ethyl groups, are removed e.g., with trimethylsilylbromide or left in place. An example of such a method is illustrated in the following scheme.

Sources & evidence

ORD record: ord-14474d8dccbd4aedb2d643abfe03b0d5
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745424B2

Reaction notes

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