Benzoyl Peroxide → Dimethyl 4-(bromomethyl)isophthalate

HRID 1685393Notes

Reaction equation

HRID 1685393 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>ClCCl.CC(=O)OCC>[Br:16][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 899711,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl ester2×HCID 516892Sodium Bicarbonate

Product 1

HCID 14920817Dimethyl 4-(bromomethyl)isophthalateYield 72.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dimethyl 4-methylisophthlate (Chemical Formula 4) (4 g, 19.2 mmol) in distilled dichloromethane were added N-bromosuccinimide (NBS, 4.8 g, 26.9 mmol) and benzoic peroxyanhydride (0.47 g, 19.2 mmol), followed by reaction at 80° C. for 24 hours in a pressure vessel with constant stirring. The reaction progress was monitored by TLC [Hex:EA=3:1]. When the reaction was detected to have reached completion, saturated NaHCO3 was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer thus formed was dried over anhydrous MgSO4, filtered and concentrated in a vacuum. The purification of the concentrate through column chromatography [Hexane: EtOAc=20:1] produced 4 g of dimethyl 4-(bromomethyl)isophthalate (Chemical Formula 5) (70%).

Workup

  1. customfollowed by reaction at 80° C. for 24 hours in a pressure vessel with constant stirring
  2. additionwas added to the reaction mixture
  3. extractionfollowed by extraction with dichloromethane
  4. customThe organic layer thus formed
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customThe purification of the
  9. concentrationconcentrate through column chromatography [Hexane: EtOAc=20:1]

Sources & evidence

ORD record
ord-3aeca7e6f54f45658f5315fd3ee41353
Source dataset
uspto-grants-2012_04
Patent number
US08148402B2

Reaction notes

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