Benzyl chloroacetate

Vicarious nucleophilic substitution (3.3.3) permits the introduction of amino groups para (or ortho if para blocked) to nitro groups by reaction with methoxyamine or 1-amino-l,2,4-triazole. In contrast, VNS substitution of 3-nitropyridine with benzyl chloroacetate proceeds at C-4. °... 

Diethyl [(benzyloxycarbonyl)methyl]phosphonate 268 A mixture of benzyl chloroacetate (18.5 g, 0.1 mole) and triethyl phosphite (18.3 g, 0.11 mole) is heated at 175° the internal temperature then rises somewhat and ethyl chloride distils off. When the exothermal reaction ceases, the mixture is heated for 1 h at 200° and then distilled in a vacuum this affords 87% (25.1 g) of a product, b.p. 148-169°/l mm. Redistillation gives analytically pure material having b.p. 174-179°/1.5 mm, nD24 1.4932. 

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