Water → 1-BROMO-5-METHOXYNAPHTHALENE

HRID 891956Notes

Reaction equation

HRID 891956 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 123363945-Bromonaphthalen-1-ol

Product 1

HCID 109006491-BROMO-5-METHOXYNAPHTHALENEYield 64%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-bromo-5-hydroxy-naphthalene (1.56 g, 7.0 mmol, prepared according to patent WO0146181), K2CO3 (1.45 g, 10.5 mmol), tetrabutylammonium chloride (15 mg, 0.05 mmol) and dimethyl sulfate (1.32 ml, 10.5 mmol) in MeCN was refluxed for 1 hour. After the addition of water, the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with water, dried over MgSO4, filtered and the solvent was removed under reduced to provide 1-bromo-5-methoxy-naphthalene (1.05 g, 64%) as a white solid, MS: m/e=236 (M+).

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionthe aqueous phase was extracted three times with CH2Cl2
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-1183b18990504a3fa1b3198d4d7d073f
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

Loading…