Azobisisobutyronitrile → Benzoic acid, 4-(bromomethyl)-2-ethoxy-, ethyl ester

HRID 2178062Notes

Reaction equation

HRID 2178062 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>FC(C1C=CC=CC=1C)(F)F>[Br:23][CH2:15][C:13]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:14]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11816602Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester

Product 1

HCID 10589339Benzoic acid, 4-(bromomethyl)-2-ethoxy-, ethyl esterYield 30.4%

Reagents, catalysts & solvents 1

HCID 27753242-MethylbenzotrifluorideSolvent

Procedure

To a solution of ethyl 2-ethoxy-4-methylbenzoate (100 mg, 0.481 mmol) in 2 mL of trifluoromethyl toluene was added NBS (94 mg, 0.529 mmol) and AIBN (10 mg) in portions. The mixture was heated to reflux and stirred for 24 h. The reaction mixture was concentrated, diluted with 10 mL of EA, washed with 5 mL of 4 N NaOH, 5 mL of brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford ethyl 4-(bromomethyl)-2-ethoxybenzoate as brown oil (42 mg, 30%), which was used for the next step directly.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with 10 mL of EA
  5. washwashed with 5 mL of 4 N NaOH, 5 mL of brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bba2b5c1b5a8455a872231d9c228d353
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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