6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.
NaH (0.31 g, 7.7 mmol, 2.0 eq.,60% in mineral oil) was washed three times with 5 mL of n-hexane. The suspension was decanted after each wash and n-hexane traces were removed under reduced pressure. Anhydrous DMF (15 mL) was then added and the suspension was stirred for 5 min. A solution of 1,2,5,6-Di-O-isopropylidene-alpha-D-glucofuranose (4, 1.00 g, 3.8 mmol, 1.0 eq.) in anhydrous DMF (15 mL) was then added dropwise. After stirring for 30 min under nitrogen flow, a solution of 1-bromo-4-chlorobutane (2.63 g, 15.4 mmol,4.0 eq.) in anhydrous DMF (5 mL) was added dropwise and the mixture was vigorously stirred for 24 hours at 40 C. The reaction mixture was then diluted in CH2Cl2 (150 mL) and washed with 0.3 N HCl (5 ¡Á 100 mL). The organic layer was dried over MgSO4 and filtered. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (CH2Cl2:EtOAc 9:1) to give 5 (0.81 g, 60% yield) as a pale yellow oil. 1H-NMR (CDCl3) delta (ppm) = 5.87 (d, J = 3.7 Hz, 1H, -CH-),4.53 (d, J = 3.8 Hz, 1H, -CH-), 4.32-4.24 (m, 1H, -CH-), 4.12-4.06 (m, 2H, -CH2-), 4.00-3.95 (m, 1H,-CH-), 3.86-3.44 (m, 5H, -CH-, -O-CH2-, -CH2-Cl), 1.84-1.60 (m, 4H, -CH2-CH2-), 1.49, 1.41, 1.34,1.31 (4 s, 12H, 4 ¡Á -CH3); 13C-NMR (CDCl3) delta (ppm) = 111.76, 108.98, 105.25, 83.05, 82.12, 81.21,72.34, 69.54, 67.39, 44.76, 29.26, 26.99, 26.80, 26.77, 26.21, 25.34; ESI-MS (ion trap): m/z 351 [M+H]+. Anal. calcd. for C16H27ClO6: C, 54.78; H, 7.76 Found: C, 54.69; H, 7.71.
The synthetic route of 6940-78-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Mattarei, Andrea; Carraro, Massimo; Azzolini, Michele; Paradisi, Cristina; Zoratti, Mario; Biasutto, Lucia; Molecules; vol. 19; 10; (2014); p. 15900 – 15917;,
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