Dichloromethane → 2,2,2-Trifluoroethyl 5-bromonaphthalene-2-sulfonate

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Reaction Steps

A round bottom flask was charged with 5-bromonaphthalene-2-sulfonyl chloride (5.00 g, 16.36 mmol) and CH2Cl2 (16.36 mL) was added. To this solution was added 2,2,2-trifluoroethanol (1.542 mL, 21.27 mmol) followed by triethylamine (3.42 mL, 24.54 mmol). The resulting solution was maintained at rt for 1 h and then concentrated. The residue was purified by MPLC using a silica gel column (80 g) using a 98:2 Heptane:EtOAc to 100% EtOAc gradient to afford 2,2,2-trifluoroethyl 5-bromonaphthalene-2-sulfonate (2.49 g, 6.75 mmol) as a white amorphous solid.

Provenance & Evidence