Dimethylformamide → Dimethyl 2-bromoterephthalate

HRID 1425933Notes

Reaction equation

HRID 1425933 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]([O-])([O-])=O.[K+].[K+].CI.CN([CH:25]=[O:26])C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([O:26][CH3:25])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68513Bromoterephthalic acid

Product 1

HCID 87741Dimethyl 2-bromoterephthalateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-bromoterephthalic acid (CIV) (5.0 g, 20.40 mmol) in DMF was added K2CO3 (7.9 g, 57.13 mmol) and CH3I (3.56 mL, 57.13 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with DCM, washed with 1 N aqueous HCl, 1 M aqueous K2CO3, 10% aqueous Na2S2O3, brine, dried over anhydrous MgSO4, and concentrated under vacuum to give dimethyl 2-bromoterephthalate (CV) (4.82 g, 17.65 mmol, 99% purity, 80% yield). ESIMS found for C10H9BrO4 m/z 275.2 (M+2H).

Workup

  1. washwashed with 1 N aqueous HCl, 1 M aqueous K2CO3, 10% aqueous Na2S2O3, brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a598557680e45caaa873de76bee6245
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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