Synthesis
GENERAL STEPS: Example A.4: Synthesis of 3-(4-bromophenyl)propanal (10×)
4-Bromophenylpropanol (4.71 g, 21.8 mmol) was dissolved in dichloromethane (DCM), Dess-Martin periodinane (9.71 g, 20.9 mmol) was added, and the reaction was carried out for 2 hours at room temperature. Upon completion of the reaction, the reaction was quenched with 2 M NaOH solution and the organic and aqueous phases were separated and the aqueous phase was extracted with DCM. The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel, the eluent being a gradient solution of DCM in cyclohexane (cHex) to afford the target product 3-(4-bromophenyl)propionaldehyde (10×) (4.46 g, 96% yield) as a colorless liquid.
1H NMR (400 MHz, CDCl3) δ 9.81 (s, 1H), 7.41 (d, J = 8.4 Hz, 2H), 7.07 (d, J = 8.4 Hz, 2H), 2.91 (t, J = 7.6 Hz, 2H), 2.79-2.74 (m, 2H).
MS (ES) C9H9BrO calculated value: 211/213, ([M-H]-) not detected, 100% purity.
References
[1] Patent: WO2015/181272, 2015, A1. Location in patent: Page/Page column 30
[2] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0120
[3] Patent: WO2015/66413, 2015, A1. Location in patent: Page/Page column 176; 177
[4] Patent: US2017/253554, 2017, A1. Location in patent: Paragraph 0425; 0426
[5] Chemical Communications, 2011, vol. 47, # 27, p. 7875 - 7877
