Uses
3-Iodophenol is used in esterification, electrophilic aromatic substitution, alkylation, nucleophilic aromatic substitution, Mitsunobu, transition metal-catalyzed cross-coupling, acylation, and oxidation reactions.
Synthesis
3-Iodophenol Synthesis:
1￡Add potassium tert-butoxide (67.3 mg, 0.60 mmol, 2.0 eq.), oxime (74.5 mg, 0.60 mmol, 2.0 eq.), and 4-bromoacetophenone (59.7 mg, 0.30 mmol, 1.0 eq.) to an oven-dry screw-cap 8mL reaction vial.
2￡Add anhydrous DMSO (1.5 mL) to the solids a magnetic stir bar.
3￡Close the vial and sparge the reaction mixture with N2 for 15 minutes, seal with parafilm.
4￡Stir the reaction mixture and heat at 100C in a metal heating block for 16 h.
5￡Dilute the mixture with CH2Cl2 or EtOAc (20 mL), pour into a mixture of water (10mL) and brine (5 mL), acidify with 10% aq HCl (~1 mL).
6￡Collect the organic phase and extract the aqueous phase with CH2Cl2 or EtOAc (3á20mL).
7￡Combine the organics, dry (MgSO4) and concentrate under reduced pressure.
8￡Purify the crude product to give 3-Iodophenol by column chromatography (30% EtOAc in hexane).
References
[1] Tetrahedron Asymmetry, 2013, vol. 24, # 13-14, p. 827 - 832
[2] Chemische Berichte, 1887, vol. 20, p. 3019
