N-bromobutanimide → HCID 22452676, compound

HRID 2185896Notes

Reaction equation

HRID 2185896 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH3:14].C1C(=O)N([Br:22])C(=O)C1>C1COCC1>[Br:22][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[C:4]([O:13][CH3:14])[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2992571,2-dimethoxynaphthalene

Product 1

HCID 22452676HCID 22452676, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To the solution of 1,2-dimethoxynaphthalene (3.83 g, 20.3 mmol) in THF (100 mL) was added dropwise at 0° C. a solution of NBS (3.62 g, 20.3 mmol) in THF (50 mL). After stirring at 0° C. for 0.5 h, the solvent was removed in vacuo and CCl4 was added. The mixture was filtered and the filtrate was concentrated. Column chromatography yielded the title compound as a yellow oil (3.72 g, 68%). 1H NMR (CDCl3) δ 8.1 (m, 2H), 7.60 (s, 1H), 7.49 (m, 2H), 3.99 (s, 3H) 3.98 (s, 3H); MS m/z 267 (M−H).

Workup

  1. customthe solvent was removed in vacuo and CCl4
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b699603df0fd4f78850183351de30738
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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