A common heterocyclic compound, 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, molecular formula is C11H13BrO2, 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. 154825-97-5.
EXAMPLE 12; 4 -R (1S)-1-[[(1S)-1-[[(1-cyanocyclopropyl)amino]carbonyl]-3-fluoro-3-methylbutyl]amino]-2,2,2- TRIFLUOROETHYLL-A, CT-DIMETHYL- (1, 1 -BI HENVLL-4-ACETIC acid; STEP 1 : 2- (4-BROMOPHENYL)-2-METHYLPROPANOIC acid; To a 0 C solution of diisopropylamine (1.52 mL) in THF (50 mL) was slowly added butyllithium (4.3 mL). The reaction mixture was stirred at 0 C for 15 minutes. It was cooled to-78 C and a solution of methyl 2- (4-bromophenyl) propanoate from Example 11 Step 2 (2.4 g) in THF (25 ML) was slowly added. The mixture was stirred at-78 C for 30 minutes. Then a solution of iodomethane (2.5 mL) in THF (25 mL) was added dropwise and the mixture was stirred at-78 C for 30 minutes then warmed up slowly to room temperature and stirred for 1 HOUR. H NMR showed 50% conversion. The reaction mixture was cooled to 0 C and 20 mL of potassium t-butoxid (1.0 M in THF) was added dropwise. The mixture was stirred at 0 C for 30 minutes, warmed up to room temperature and stirred for 1 hour. The reaction mixture was poured into ice (50 g) and saturated aqueous ammonium chloride (100 mL), extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo to yield a residue which was diluted with THF (30 ML) and methyl alcohol (15 mL). The solution was cooled to 0 C and 20 mL of lithium hydroxide (1.0 N) was added. The mixture was stirred at room temperature for 3 hours. Then the reaction mixture was poured into ice and 1N HC1 and extracted with dichloromethane (2 x 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound. ‘H NMR (CD3COCD3) 8 10.85 (1H, bs), 7.53 (2H, d), 7.48 (2H, d), 1.50 (6H, s).
The synthetic route of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/19161; (2005); A1;,
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