N-bromobutanimide → 1-Bromo-6-methoxynaphthalen-2-ol

HRID 1771472Notes

Reaction equation

HRID 1771472 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:21][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[OH:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 184287461-Bromo-6-methoxynaphthalen-2-olYield 72.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-methoxynaphthalen-2-ol (2.00 g, 11.5 mmol) in DMF (20 mL) was added NBS (2.15 g, 12.1 mmol) and the reaction mixture was stirred at 25° C. for 4 hours. The resulting mixture was diluted with EtOAc (300 mL), washed with H2O (100 mL×5) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product, which was purified by silica gel column (PE/EtOAc=20/1) to give the product (2.10 g, yield 72%).

Workup

  1. washwashed with H2O (100 mL×5) and brine (100 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product, which
  5. customwas purified by silica gel column (PE/EtOAc=20/1)

Sources & evidence

ORD record
ord-8b77cb8b509f4c2394d63e67f4bd76b6
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

Loading…