Facile Chlorination of Benzyl Alcohols Using 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and Sulfonyl Chlorides

Table 2. Chlorination of three benzyl alcohols using DBU and sulfonylating agents a HO Cl DBU (2 eq.) TsCl or MsCl (1.5 eq.) CH 2 Cl 2 , 0 o C-> rt 10 min X X 2 Entry X Sulfornyl chloride Chloride Yield (%) b δ of Benzylic H Alcohol Chloride 2 1 NO2 TsCl 2a 81 4.84 4.66 2 NO2 MsCl 2a 69 3 H T sCl 2b 59 4.63 4.55 4 H MsCl 2b 65 5 OMe TsCl 2c 44 4.60 4.57 6 OMe MsCl 2c 79 a Benzyl alcohols (1.32 -1.36 mmol) were used with 10 -15 mL CH2Cl2.b Isolated yields.