Ethyl Acetate → 4-Bromomethyl-2-phenylbenzoic acid

HRID 2121202Notes

Reaction equation

HRID 2121202 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:17][CH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 154962685-Methylbiphenyl-2-carboxylic acid

Product 1

HCID 234364554-Bromomethyl-2-phenylbenzoic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-methyl-2-phenylbenzoic acid (1.66 g, 7.82 mmol), prepared as in Example 227B, N-bromosuccinimide (1.40 g, 8.21 mmol) and 2,2′-azobisisobutyronitrile (25 mg) in carbon tetrachloride (30 mL) was stirred at reflux for 1 hour. The reaction mixture was poured into ethyl acetate and extracted with water (3×) and brine, dried, filtered, and concentrated in vacuo to give 4-bromomethyl-2-phenylbenzoic acid (2.26 g).

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with water (3×) and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5812b1cdb544d51b24838f07d3ed500
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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