Hydrochloric Acid → HCID 59596558, compound

Participants

Reaction Conditions

Reaction Steps

A solution 4-bromo-2-fluoro-phenol (75 g, 0.39 mol) in THF (750 mL) was cooled to −78° C. and treated dropwise with n-butyllithium (471 mL, 2.5M solution) over 1 hour keeping the internal temperature below −60° C. After stirring for a further 30 minutes the mixture was treated with chlorotrimethylsilane (128 g, 1.18 mol) in THF (150 mL) over 30 minutes keeping the internal temperature below −60° C. After the addition the mixture was allowed to warm to 0° C. over 40 minutes. The mixture was poured into 1M hydrochloric acid and the layers separated. The aqueous layer was extracted with diethyl ether (×2) and the combined organic layers were washed with water, brine, dried (MgSO4) and concentrated in vacuo to give a colourless liquid. The liquid was dissolved in THF (750 mL) and treated with tetrabutylammonium fluoride (393 mL, 1M solution in THF). After 5 minutes the solution was poured into water and the layers separated. The aqueous layer was extracted with diethyl ether (×2) and the combined organic layers washed with water, brine, dried (MgSO4) and evaporated to a straw-coloured oil. The oil was dissolved in DCM/cyclohexane (1:1, 500 mL) and stirred with silica (15 g) and filtered. The filtrate was evaporated to give the title compound as an oil which solidified on standing (72 g, 100% yield). 1H NMR (CDCl3) 7.04-6.92 (2H, m), 6.92-6.76 (1H, m), and 0.077 (9H, s).

Provenance & Evidence