Application of 7745-91-7, A common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, molecular formula is C7H8BrN, 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.
Example 2; (3’R,4’S,5’S,6’R,7S)-1-[(4-ethylphenyl)methyl]-6′-hydroxymethyl-3′,4′,5′,6′-tetrahydro-spiro[furo[3,4,f]indole-7(5H),2′-[2H]pyran]-3′,4′,5′-triol; 1) Synthesis of (3-bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine; [Show Image] Under a nitrogen stream, a mixture of 3-bromo-4-methyl-phenylamine (4.94 g, 26.55 mmol), bromoacetaldehyde diethyl acetal (6.80 g, 34.50 mmol), triethylamine (5.37 mL, 38.53 mmol) and ethanol (10.3 mL) was stirred for 2 hours at 150C using a microwave apparatus. The resultant solution was cooled to room temperature, and then water was added thereto. The resultant mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution = ethyl acetate:n-hexane (1:10)), to thereby obtain the titled compound (6.43 g, 80%). 1H-NMR (CDCl3) delta: 1.17-1.28 (6H, m), 2.27 (3H, s), 3.18-3.77 (6H, m), 3.80 (1H, bs), 4.61-4.68 (1H m), 6.49 (1H, dd, J = 2.47, 8.23 Hz), 6.83 (1H, d, J = 2.47 Hz), 6.99 (1H d, J = 8.23 Hz).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP2048152; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary