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Preparation of difluorophosphonoacetic acid and its derivatives

, : Preparation of difluorophosphonoacetic acid and its derivatives. Journal of Organic Chemistry 53(7): 1523-1527

The preparation of ethyl difluoro(diethoxyphosphinyl)acetate (1) has been effected by the acylation of [(diethoxyphosphinyl)difluoromethyl]zinc bromide with ethyl chloroformate in the presence of a catalytic amount of cuprous bromide. Similarly prepared were ethyl dilfuoro)diethoxyphosphinyl)pyruvate (2) and N,N-diethyldifluoro(diethoxyphosphinyl)acetamide (3). Bromotrimethylsilane selectively reacted with 1 to yield ethyl difluoro[bis(trimethylsiloxy)phosphinyl]acetate (9).The remaining ethyl carboxylic ester of 9 reacted with iodotrimethylsilane to produce trimethylsilyl difluoro[bis(trimethylisiloxy)phosphinyl]acetate (10), which was subsequently hydrolyzed to yield difluorophosphonoacetic acid (8). The phosphonate 9 was gently chlorinated to yield ethyl difluoro(dichlorophosphinyl)acetate (11).

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Accession: 006173055

DOI: 10.1021/jo00242a034

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