Water → 1,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

HRID 1771710Notes

Reaction equation

HRID 1771710 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([C:8]([OH:10])=O)[CH:7]=1.[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI.O.CN([CH:26]=[O:27])C>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:27][CH3:26])=[O:10])[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 900735-Bromoisophthalic acid

Product 1

HCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterYield 90%

Procedure

5-bromobenzene-1,3-dicarboxylic acid (5 g, 20.4 mmol, 1.0 eq) was dissolved in DMF (150 mL). Cs2CO3 (33.2 g, 102 mmol, 5.0 eq) was added and the reaction stirred for 30 min. MeI (7.2 g, 51 mmol, 2.5 eq) was added dropwise and the solution was stirred at room temperature overnight. Water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (5 g, 90%).

Workup

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8aff085d8008475182b4e25c7cc504a1
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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