Carbon Dioxide → 3-Bromo-2-methylbenzoic Acid

Participants

Reaction Steps

To a solution of 1,3-dibromo-2-methylbenzene (6.57 g) in dry THF (100 mL), t-BuLi solution (1.5 M in pentane, 17 mL) was added dropwise at −80° C. After addition, the reaction mixture was stirred between −76˜−78° C. for 2 h. After the mixture was cooled to below −80° C., dry ice was added, and then warmed to room temperature naturally. Solvent was removed, 5% NaOH solution (40 mL) was added, washed with CH2Cl2 (10 mL×2). Then the aqueous layer was acidified with concentrated HCl to pH=1, extracted with EtOAc (100 mL×2). The combined organic phase was dried over anhydrous Na2SO4. After removing the solvent, the residue was purified by silica column chromatography, (eluted with petrol ether:EtOAc=8:1 to 1:1), to obtain 3.58 g of the product. Yield: 63.4%. 1H NMR (400 MHz, CDCl3): δ 2.73 (s, 3 H), 7.15 (t, J=8.0 Hz, 1 H), 7.77 (dd, J=8.0 Hz, J=1.2 Hz, 1 H), 7.94 (dd, J=8.0 Hz, J=1.2 Hz, 1 H).

Provenance & Evidence