2-Bromomethylnaphthalene → HCID 17902008, compound

HRID 1713277Notes

Reaction equation

HRID 1713277 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C)C=O>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][N:17]1[C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]2[C:13]1=[O:23]

Participants

4

Reactant 2

HCID 703202-BromomethylnaphthaleneHCID 24194345Phthalimide potassium salt

Product 1

HCID 17902008HCID 17902008, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(bromomethyl)naphthalene (0.500 g) in N,N-dimethylformamide (11 mL) was added potassium phthalimide (0.461 g), and the resulting mixture was stirred at 50° C. for 2 hours. The reaction mixture was partitioned between ethyl acetate (50 mL) and water (15 mL). The organic layer was washed successively with water (15 mL×2) and brine (15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.380 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 mL) and water (15 mL)
  2. washThe organic layer was washed successively with water (15 mL×2) and brine (15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7806e4d73b9442e6996ce42e81372731
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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