N-bromobutanimide → Dimethyl 4-(bromomethyl)isophthalate

HRID 1987345

Reaction equation

HRID 1987345 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 residure 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 residure was purified via column chromatography on silica gel (hexanes

Sources & evidence

ORD record
ord-bf2451e45c6c4d52a38fdd569c7471e7
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Linked notes

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