Benzaldehyde → HCID 81697470, 화합물

To a solution of 1-bromo-4-iodo-2-(trifluoromethyl)benzene (246 mg, 0.701 mmol) in 1.4 mL of Et2O (C=0.5M) was added dropwise a 1.6M solution of BuLi in hexane (460 μL, 1.05 eq) at −78° C. After 15 min of stirring, benzaldehyde (86 μL, 1.2 eq) was slowly added. The mixture was stirred for 4 h at −75° C. and then, 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 93:7 to 90:10) to afford the desired product in 76% yield (176 mg) as an uncoloured oil. 1H NMR (300 MHz, CDCl3) δ 7.76 (d, J=2.2 Hz, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.41-7.27 (m, 6H), 5.81 (s, 1H), 2.36 (s, OH); 13C NMR (75 MHz, CDCl3) δ 143.5 (C), 142.8 (C), 135.1 (d, J=2.0 Hz, CH), 131.0 (CH), 130.2 (q, J=31.3 Hz, C), 129.0 (CH), 128.5 (CH), 126.7 (CH), 125.9 (q, J=5.4 Hz, CH), 123.0 (q, J=273.6 Hz, C), 118.9 (q, J=2.0 Hz, C), 75.4 (CH); MS (ESI) m/z: 313.0, 315.0 [M-OH, 79Br, 81Br]+; 348.0, 350.0 [M+NH4, 79Br, 81Br]+; 680.0 [2M+NH4, 79Br, 81Br]+.

1. stirringThe mixture was stirred for 4 h at −75° 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 93:7 to 90:10)

ORD 기록

ord-7359f5da692d4aed859fe94fdb4ed21b

출처 데이터셋

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09428500B2