Application of 2606-51-1,Some common heterocyclic compound, 2606-51-1, name is 5-(Bromomethyl)benzo[d][1,3]dioxole, molecular formula is C8H7BrO2, 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.
To a round-bottomed flask equipped with a reflux condenser and capped with a rubber septum were added (R)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (2a) (0.6 mmol, 124 mg), potassium carbonate (1.2 mmol, 166 mg), anhydrous acetone (25 mL), and 5-(bromomethyl)benzo[d]-1,3-dioxole (3) (0.9 mmol, 194 mg). The mixture was refluxed under stirring and nitrogen atmosphere for 24 h. Afterwards, a saturated aqueous solution of NaCl (25 mL) was added to the mixture, which was extracted with CH2Cl2 (3 x 50 mL). The organic phase was dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane/ethyl acetate (1:1) as eluent, affording the desired product 1a. Yield: 174 mg (85%); [alpha]D20 = +18.6o (c = 0.05 g/100 mL CHCl3) ([alpha]D lit.13 = +18o (c = 0.05 g/100 mL CHCl3)); off-white solid; m.p. 120-121 oC; Rf = 0.35 (eluent: dichloromethane/ethyl acetate (1:1)); 1H NMR (300 MHz, CDCl3): delta 6.94 (s, 1H), 6.77 (q, J = 9.1 Hz, 2H), 6.55 (d, J = 11.5 Hz, 2H), 5.91 (s, 2H), 3.83-3.75 (m, 7H), 3.69 (d, J = 13.4 Hz, 1H), 3.59 (d, J = 13.4 Hz, 1H), 3.04 (ddd, J = 12.8, 8.4, 3.7 Hz, 1H), 2.81 (ddd, J = 15.4, 9.4, 5.7 Hz, 1H), 2.69 (dt, J = 12.0, 4.5 Hz, 1H), 2.57 (dt, J = 15.8, 3.9 Hz, 1H), 1.35 (d, J = 6.7 Hz, 3H); 13C NMR (75 MHz, CDCl3): delta 147.6, 147.2, 147.1, 146.3, 133.4, 132.1, 126.0, 121.5, 111.3, 110.3, 109.0, 107.7, 57.7, 55.8, 55.7, 55.5, 43.5, 26.6, 19.9; IR (KBr, cm-1) 2922.2, 2852.7, 1500.6, 1487.1, 1438.9, 1367.5, 1242.2, 1224.8; GC/MS (m/z, %): 341 (1.0), 135 (100.0), 326 (74.4), 327 (16.6).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Bromomethyl)benzo[d][1,3]dioxole, its application will become more common.
Reference:
Article; Correa, Bianca K.; Silva, Tamiris R.C.; Raminelli, Cristiano; Tetrahedron Letters; vol. 59; 39; (2018); p. 3583 – 3585;,
Bromide – Wikipedia,
bromide – Wiktionary