Dimethylformamide → Dimethyl 3-bromophthalate

Reaction equation

[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]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 516892Sodium Bicarbonate

HCID 112995633-bromophthalic Acid

Product 1

HCID 53438518Dimethyl 3-bromophthalateYield 86%

Conditions

Temperature: 70 °C

Procedure

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).