4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-(3-bromophenyl)butyl ester

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Reaction Steps

A cold (0° C.) solution of 4-(3-bromophenyl)butan-1-ol (1.08 g, 4.7 mmol) and p-toluenesulfonyl chloride (1.2 g, 6.3 mmol) in THF was treated slowly with triethyl amine (1.8 mL, 12.3 mmol), stirred at room temperature for 4 hours, poured into cold saturated aqueous NH4Cl and extracted with ether. The organic extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue on silica gel (ISCO) using (hexanes/EtOAC 9.5/0.5) as the eluting solvent afforded toluene-4-sulfonic acid 4-(3-bromophenyl)-butyl ester as a colorless oil (2.4 g, 76% yield). m/e (M+NH4)+ 400.1. 1H NMR (400 MHZ, DMSO-d6) δ ppm, 1.4-1.6 (m, 4 H), 2.4 (s, 3 H), 2.4-2.5 (m, 2 H), 4.0 (t, J=6.0 Hz, 2 H), 7.2 (t, J=7.8 Hz, 1 H), 7.3-7.3 (m, 1 H), 7.3-7.3 (m, J=8.0, 1.0 Hz, 1 H), 7.4-7.5 (m, J=8.6 Hz, 2 H), 7.7-7.8 (m, 2 H).

Provenance & Evidence