Diethyl Sulfate → 2-Bromo-7-ethoxynaphthalene

HRID 891957

Reaction equation

HRID 891957 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([OH:12])=[CH:9]2)=[CH:4][CH:3]=1.S(OCC)(O[CH2:17][CH3:18])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][C:8]([O:12][CH2:17][CH3:18])=[CH:7][CH:6]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 6138277-Bromo-2-naphthol

Product 1

HCID 222401492-Bromo-7-ethoxynaphthaleneYield 89%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-bromo-naphth-2-ol (1.0 g, 4.5 mmol, prepared according to patent WO 0146187 A1) in acetonitrile (10 ml) was added diethyl sulfate (1.04 g, 6.7 mmol), K2CO3 (0.92 g) and tetrabutylammonium bromide (10 mg). The reaction mixture was refluxed for 1 hour, poured on water and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to provide 2-bromo-7-ethoxynaphthalene (89%), MS: m/e=252 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. additionpoured on water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-258293cb967e432aaa11dcbe01b4630c
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Linked notes

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