Methanol → (4-Amino-3,5-dichlorophenyl)methanol

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Methanol (400 ml) was added dropwise over 2 hours to a mixture of methyl-3,5-dichloro-4-aminobenzoate (110 g), NaBH4 (142.5 g) and t-butanol (1.1 L). At the end of the addition, the mixture was refluxed 3 hours, cooled, then H2O (1.2 L) was carefully added. The resulting layers were separated and the organic phase was washed with H2O (2×200 mL), separated, dried (MgSO4), filtered and evaporated to afford the desired product (89 g), mp 110-112° C.

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