N-bromobutanimide → Dimethyl 4-(bromomethyl)isophthalate

HRID 1784195Notes

Reaction equation

HRID 1784195 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[Br:16]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([CH2:14][Br:16])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 899711,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl ester

Product 1

HCID 14920817Dimethyl 4-(bromomethyl)isophthalate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methyl-isophthalic acid dimethyl ester (1.06 g, 5.10 mmol), N-bromosuccinimide (1.00 g, 5.61 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (0.31 g, 1.27 mmol) were suspended in carbon tetrachloride (22 mL) and the resulting mixture was refluxed for 16 hours under N2. The orange solution was concentrated under reduced pressure and the resulting orange residue was purified via column chromatography on silica gel (hexanes:EtOAc, 7:1, v/v). 4-Bromomethyl-isophthalic acid dimethyl ester was isolated as a yellow crystalline solid (1.05 g, 72%). 1H NMR (CDCl3) δ 3.95 (s, 3H), 3.97 (s, 3H), 4.96 (s, 2H), 7.57 (d, 1H, J=9.0 Hz), 8.13 (dd, 1H, J=9.0, 3.0 Hz), 8.62 (d, 1H, J=3.0 Hz).

Workup

  1. temperaturethe resulting mixture was refluxed for 16 hours under N2
  2. concentrationThe orange solution was concentrated under reduced pressure
  3. customthe resulting orange residue was purified via column chromatography on silica gel (hexanes

Sources & evidence

ORD record
ord-da4dcd5cf6f748469c422da922640649
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

Loading…