Dimethylformamide → Dimethyl 3-bromophthalate

反応式

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4](C(O)=O)[C:3]=1[C:11]([OH:13])=[O:12].I[CH3:15].[C:16](=[O:19])(O)[O-].[Na+].CN([CH:24]=[O:25])C>>[CH3:16][O:19][C:24](=[O:25])[C:4]1[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=1)[C:11]([O:13][CH3:15])=[O:12]

参加物

反応物 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 516892Sodium Bicarbonate

HCID 112995633-bromophthalic Acid

生成物 1

HCID 53438518Dimethyl 3-bromophthalate収率 86%

反応条件

温度: 70 °C

実験手順

To a stirred solution of 3-bromophthalic acid (2.5 g, 10 mmol) in DMF (20 mL), were added iodomethane (3.1 g, 22 mmol) and sodium bicarbonate (1.8 g, 22 mmol). The mixture was heated to 70° C. with stirring for 26 hours. The solvent was evaporated in vacuo, and the residue was partitioned between diethyl ether (100 mL) and water (100 mL). The organic phase was washed with sat. sodium bicarbonate (100 mL) and brine (100 mL), and dried (MgSO4). The solvent was evaporated in vacuo, and dried under high vacuum to afford 2.4 g (86%) of the product as a white solid: 1H NMR (DMSO-d6) δ 3.84 (s, 3H), 3.86 (s, 3H), 7.57 (t, J=8.0 Hz, 1H), 8.01 (d, J=8.1 Hz, 2H).