Bromobenzene → (3-(Phenylamino)phenyl)methanol

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A solution of Tris(dibenzylideneacetone)dipalladium(0) (0.178 g, 0.19 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol) in THF (20 mL) (degassed) was heated to 50 ºC under a nitrogen atmosphere for 30 min. (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) (0.4 g, 3.25 mmol) and cesium carbonate (2.117 g, 6.50 mmol) were added followed by bromobenzene (0.409 mL, 3.90 mmol) and the mixture stirred at 65 °C over two days. The reaction mixture was cooled to room temperature then diluted with DCM and filtered. stirred with SiliCycle SiliMet-SH (1 g) for 3 h at 60 °C. The mixture was filtered through an acrodisc glassfiber filter, 25 mm, 1.0 µm. The filtrate (clear) was concentrated to give crude product (1,00 g). The crude was dissolved in DMSO and the product was purified by prep-HPLC on a Kromasil C8 column (10 µm 250x50 ID mm) using a gradient of 5-65% acetonitrile in H2O/ACN/HOAc 95/5/0.2 buffer over 30 minutes with a flow of 100 mL/min. The compounds were collected on UV at 303 nm, threshold 1000. The product containing fractions were pooled and concentrated on the rotavapor. Toluene was added and evaporated to get rid of residue of water to give the product (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) as a transparent oil.

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