Electric Literature of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
[0115] To a stirred solution of (Z)-4-(l-(4-(methoxymethoxy)phenyl)-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde (12 g, 28.4 mmol, with – 10- 15% of another regioisomer) in 2-methyltetrahydrofuran (120 mL) were added 2-chloro-4- fluoro-l-iodobenzene (5.5 mL, 40.5 mmol) and KOH (45 mL, 3M aqueous solution, 142.2 mmol). The resultant mixture was degassed with argon for 10 min followed by the addition of PdCl2(PPh3)2 (0.7 g, 2.84 mmol). After stirring at 60C for 12 h, the mixture was cooled to rt and quenched with water:EtOAc (1 : 1, 100 mL). The organic layer was separated, washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The crude compound was purified by chromatography (Si02, 10% EtOAc/hexane) to afford (E)-4-(2-(2- chloro-4-fluorophenyl)- 1 -(4-(methoxymethoxy) phenyl) but- 1 -en- 1 -yl)benzaldehyde as a pale yellow solid (6.0 g, 67% with -10-15% of the other regioisomer). Major isomer: XH NMR (400 MHz, CDC1 ) delta 9.84 (s, 1H), 7.55 (d, = 8.0 Hz, 2H), 7.20 – 7.17 (m, 2H), 7.10 (d, = 8.0 Hz, 2H), 7.04 – 6.97 (m, 4H), 6.84 – 6.80 (m, 1H), 5.19 (s, 2H), 3.50 (s, 3H), 2.55 – 2.45 (m, 2H), 0.97 – 0.93 (m, 3H); MS (ESI) m/z 425.19 [M+H]+.
The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HEGDE, Sayee, Gajanan; HOPKINS, Chad, Daniel; (76 pag.)WO2019/23481; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com