Tert-Butyl nitrite → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

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To a stirred suspension of 4-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine (41 g, 130 mmol, 1 eq.) in 2000 ml of MeCN, were added sodium bromide (40.1 g, 390 mmol, 3 eq.), Copper (I) bromide (18.65 g, 130 mmol, 1 eq.) and t-Butylnitrite (16.38 g, 143 mmol, 1.1 eq.). The reaction was slowly heated to 80° C. for 1 h and allowed to cool. MeCN was evaporated and 500 ml water/1000 ml DCM were added to the residue. The crude was triturated, filtered through “celite” plug and washed with further 500 ml of EtOAc. The organic layers were combined, dried over MgSO4, and evaporated to give N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (36 g, 69% yield, 10:1 mixture of stereoisomers) as a brown viscous oil.

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