Iodine → (4'-Chloro-4-ethylbiphen-3-yl)furan-2-ylmethanol

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Reaction Steps

Approximately 10 ml of a solution of 3-bromo-4′-chloro-4-ethylbiphenyl (40.0 g, 135.3 mmol) in tetrahydrofuran (200 ml) is added to magnesium turnings in a dry flask, followed by a crystal of iodine. The mixture is allowed to stand without stirring for 30 minutes, then stirred once and warmed until the orange coloured mixture becomes colourless. The remainder of the 3-bromo-4′-chloro-4-ethylbiphenyl solution is added dropwise over 30 minutes with external heating applied as necessary to maintain a gentle reflux. Once the addition is complete, the mixture is heated to reflux for 2-3 hours, until only trace residues of magnesium remain. The mixture is cooled to room temperature, and then cooled further in an ice-bath. A solution of 2-furaldehyde (13.05 g, 135.8 mmol) in tetrahydrofuran (80 ml) is added dropwise over 35 minutes, and the mixture is stirred at room temperature overnight.

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