Benzaldehyde → HCID 62689316, compound

To a solution of 1,4-dibromo-2-(trifluoromethyl)benzene (300 mg, 0.987 mmol) in 2 mL of Et2O (C=0.5M) was added dropwise a 1.6M solution of BuLi in hexane (650 μL, 1.05 eq) at −78° C. After 25 min of stirring, benzaldehyde (120 μL, 1.2 eq) was slowly added. The mixture was stirred for 2 h at −78° C. and was allowed to warm to r.t. overnight. Then, the reaction mixture was hydrolyzed with water and with a 1M HCl solution to acidify. The layers were separated. The aqueous layer was extracted with DCM (3×10 mL). The combined organics were washed with brine, dried over MgSO4, filtered and solvents were removed in vacuo. The crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 95:5) to afford the desired product in 90% yield (295 mg) as uncoloured oil. 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=2.1 Hz, 1H), 7.67 (dd, J=8.4, 2.1 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.39-7.27 (m, 5H), 6.24 (s, 1H), 2.44 (s, OH); 13C NMR (75 MHz, CDCl3) δ 142.3 (C), 141.4 (q, J=1.4 Hz, C), 135.5 (CH), 131.5 (CH), 129.3 (q, J=30.9 Hz, C), 128.8 (q, J=6.1 Hz, CH), 128.7 (CH), 128.0 (CH), 126.5 (CH), 123.5 (q, J=274.6 Hz, C), 121.7 (C), 70.6 (q, J=2.1 Hz, CH); MS (ESI) m/z: 375.0, 377.0 [M−H+HCO2H, 79Br, 81Br]−; 705.2, 707.2 [2M−2H+HCO2H, 79Br, 81Br]−.

1. stirringThe mixture was stirred for 2 h at −78° C.
2. customThe layers were separated
3. extractionThe aqueous layer was extracted with DCM (3×10 mL)
4. washThe combined organics were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customsolvents were removed in vacuo
8. customThe crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 95:5)

ORD record

ord-8198e8df27c84be6b2908299e8ac29e6

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428500B2