Selective ortho-chlorination of phenol using sulfuryl chloride in the presence of t-butylaminomethyl polystyrene as a heterogeneous amine catalyst

Reaction of phenol with sulfuryl chloride in the presence of a catalytic amount of the heterogeneous amine catalyst, t-butylaminomethyl polystyrene, in a nonpolar solvent, proceeds with high conversion (∼98%) and with high selectivity (∼89%) to ortho-chlorophenol. The catalyst is stable under the chlorination conditions, and can easily be regenerated by filtration and reused. This method could be applicable to other phenols.