Dimethylformamide → Dimethyl 3-bromobenzene-1,2-dicarboxylate

HRID 448320Notes

Reaction equation

HRID 448320 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

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 112995633-bromophthalic Acid

Product 1

HCID 53438518Dimethyl 3-bromobenzene-1,2-dicarboxylateYield 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).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between diethyl ether (100 mL) and water (100 mL)
  3. washThe organic phase was washed with sat. sodium bicarbonate (100 mL) and brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-37f4f7330abd48b1b60d80bcb57c004e
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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