α-(4-Bromophenyl)-2-pyridinemethanol Chemical Properties

Boiling point:

394.5±32.0 °C(Predicted)

Density 

1.496±0.06 g/cm3(Predicted)

pka

12.46±0.20(Predicted)

α-(4-Bromophenyl)-2-pyridinemethanol Usage And Synthesis

Synthesis

α-(4-Bromophenyl)-2-pyridinemethanol was synthesised from 4-bromobenzaldehyde and 2-iodopyridine^[1]. Yield: 75%. The specific reaction steps are as follows:
(1) Charge an oven dried vial with a magnetic stirring bar, indium powder (34.4mg, 0.30mmol, 1.5 equiv) and (±)-10-camphorsulfonic acid(11.6 mg, 0.050 mmol, 25 mol%).
(2) Seal the vial evacuated and backfill with N2(3 cycles).
(3) Add dry THF (2.0mL) to this follow by 4-bromobenzaldehyde(37mg,0.20mmol) and 2-iodopyridine (43 μL, 0.40mmol, 2 equiv) through micro syringe.
(4) Heat the reaction vial at 70°C with vigorous stirring for 8h.
(5) Cool the crude reaction mixture and dilute with CH2Cl2(20 mL), add 10% aq.NaOH (15 mL).
(6) Stir the resultant mixture vigorously for 10 min, until the aqueous layer appear cloudy white.
(7) Extract the aqueous ph ase with CH2Cl2(3 × 10 ml).
(8) Dry the combine organic extracts over anhydrous Na2SO4, filter and concentrate in vacuo.
(9) Purification by flash column chromatography (10-30% EtOAc in 40-60 PE).

References

[1] MATTHEW, GAUNT, ALEX, et al. Modular synthesis of heterobenzylic amines via Carbonyl Azinylative Amination[J]. ChemRxiv, 2024, 115 1. DOI:10.26434/chemrxiv-2024-rlfnp.