tert-butyl-[(2-iodophenyl)methoxy]-dimethylsilane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 2-iodobenzylalcohol (2.34 g, 10 mmol) in 50 mL DMF was added imidazole (1.02 g, 15 mmol, 1.5 equiv) and TBSCl (1.66 g, 11 mmol, 1.1 equiv). The mixture was stirred at room temperature for 5 h, then 40 mL of water was added. The mixture was transferred to a separatory funnel. The aqueous layer was separated and extracted with ether (2×40 mL). The combined organic layers were then washed with water (2×40 mL), dried with MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography and then Kugelrohr distillation to afford the product (3.107 g, 89%) as a clear colorless liquid. The mixture was transferred to a separatory funnel The aqueous layer was separated extracted with ether (2×40 mL) The combined organic layers were then washed with water (2×40 mL) dried with MgSO4 filtered The solvent was removed in vacuo the residue was purified by column chromatography Kugelrohr distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 2-iodobenzylalcohol (2.34 g, 10 mmol) in 50 mL DMF was added imidazole (1.02 g, 15 mmol, 1.5 equiv) and TBSCl (1.66 g, 11 mmol, 1.1 equiv). The mixture was stirred at room temperature for 5 h, then 40 mL of water was added. The mixture was transferred to a separatory funnel. The aqueous layer was separated and extracted with ether (2×40 mL). The combined organic layers were then washed with water (2×40 mL), dried with MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography and then Kugelrohr distillation to afford the product (3.107 g, 89%) as a clear colorless liquid. The mixture was transferred to a separatory funnel The aqueous layer was separated extracted with ether (2×40 mL) The combined organic layers were then washed with water (2×40 mL) dried with MgSO4 filtered The solvent was removed in vacuo the residue was purified by column chromatography Kugelrohr distillation