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(32 mmol) and ammonium thiocyanate (31.6 mmol) in CH Cl2
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(30 mL) and the mixture was heated to reflux with stirring. The
progress of the reaction was monitored by TLC (n-hexane–
EtOAc, 7:3). For ultrasonically assisted reactions, the reaction
mixture was ultrasonicated in a TCL (BIO-Technics India) soni-
cator and the progress of the reaction was followed by TLC.
Upon completion of the reaction, the mixture was filtered, and
the organic layer was washed with brine, dried over anhydrous
Na SO , filtered, and the solvent was removed. The residue was
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purified by chromatography on silica (n-hexane–EtOAc) to
afford 2-thiocyanatophenol. Yield: 90% (thermal) and 92%
1
(ultrasonication). H NMR (CDCl ): δ = 7.14 (d, J = 8.1 Hz, 1 H),
3
6.73 (m, J = 7.9 Hz, 2 H), 6.54 (d, J = 8.1 Hz, 1 H), 4.83 (s, 1 H).
MS: m/z = 151.
16912.
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Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, 237–240