1-Bromo-3-chloropropane → Methyl 4-(3-chloropropylthio)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-sulfanylbenzoate (2.00 g, 11.9 mmol) in N,N-dimethylformamide (13 mL) was added potassium carbonate (6.57 g, 47.6 mmol) and 1-bromo-3-chloro-propane (2.35 mL, 23.8 mmol). The mixture was heated at 60° C. for 16 h. The reaction mixture was filtered and the solvent removed in vacuo. The material was dissolved in dichloromethane (10 mL) and washed with water (3×10 mL) and a saturated aqueous NH4Cl (10 mL). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. Silica gel chromatography (0-100% dichloromethane/hexane) provided methyl 4-(3-chloropropylsulfanyl)benzoate (1.87 g, 64%) as a colorless viscous liquid. ESI-MS m/z calc. 244.0. Found 245.1 (M+1)+; Retention time: 1.83 minutes (3 min run). 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.2 Hz, 2H), 3.84 (s, 3H), 3.79-3.61 (m, 2H), 3.18 (t, J=7.2 Hz, 2H), 2.20-1.97 (m, 2H).

Provenance & Evidence