N-bromobutanimide → 4-(bromomethyl)naphthalene-1-carboxylic Acid

HRID 1166735Notes

Reaction equation

HRID 1166735 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:15][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 30142854-Methyl-1-naphthalenecarboxylic acid

Product 1

HCID 109783504-(bromomethyl)naphthalene-1-carboxylic AcidYield 111.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-methylnaphthoic acid (10 g, 54 mmol), N-bromosuccinimide (10 g, 56 mmol) and AIBN (100 mg) in CCl4 (250 mL) was refluxed for 3 hr. The reaction mixture was concentrated and dissolved in ethyl acetate. The organic layer was washed with water, brine and dried over MgSO4. Evaporation of the solvent gave the desired product (16 g, 80%).

Workup

  1. temperaturewas refluxed for 3 hr
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3fe04e35517b4c8f9524c476bae20b15
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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