Methanol → Methyl 4-bromo-2-fluoro-5-methylbenzoate

반응식

[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.O=S(Cl)Cl.[CH3:17]O>>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([F:12])[CH:3]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 341745874-Bromo-2-fluoro-5-methylbenzoic acid

생성물 1

HCID 66817979Methyl 4-bromo-2-fluoro-5-methylbenzoate

반응 조건

온도: 80 °C

실험 절차

To a solution of 4-bromo-2-fluoro-5-methylbenzoic acid (i-2a) (1.87 g, 8 mmol) in CH3OH (50 mL) at 0° C. was added SOCl2 (6 mL, 80 mmol) dropwise. Then the mixture was heated to 80° C. for 2 h. The solvent was removed in vacuo and the residue was diluted with EtOAc and washed with H2O, brine, dried over anhydrous Na2SO4, and concentrated. The resulting crude solid was washed with PE to give the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, d), 7.37 (1H, d), 3.92 (3H, s), 2.39 (3H, s).