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

HRID 401178Notes

Reaction equation

HRID 401178 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-74b5e9fac6714a19abcc4a0475217cf5
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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