Diethyl Ether → (R)-1-(1-(Benzyloxy)-3-fluoropropan-2-yl)-4-bromo-2-methylbenzene

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Reaction Conditions

Reaction Steps

To 24A (0.74 g, 1.790 mmol) in tBuOH (10 mL) was added TBAF (1.0 M in THF, 5.37 mL, 5.37 mmol). The mixture was stirred at 80° C. for 2 h. Ethyl ether was added and the mixture was filtered. The filtrate was evaporated and the crude product was purified by flash chromatography (0-30% EtOAc/hexanes) to give 24B (0.46 g, 1.364 mmol, 76% yield) as colorless oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.27-7.43 (m, 7H) 7.13 (d, J=8.34 Hz, 1H) 4.74 (d, J=5.56 Hz, 1H) 4.62 (d, J=5.56 Hz, 1H) 4.47-4.59 (m, 2H) 3.71-3.81 (m, 1H) 3.60-3.70 (m, 1H) 3.37-3.57 (m, 1H) 2.33 (s, 3H); 19F NMR (376 MHz, chloroform-d) δ ppm −224.19 (s, 1F).

Provenance & Evidence