Benzyl Bromide → 2-(Benzyloxy)-6-bromonaphthalene

HRID 2307190Notes

Reaction equation

HRID 2307190 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:13]([O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 6405952-(Benzyloxy)-6-bromonaphthalene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mechanically stirred mixture of 6-bromonaphth-2-ol (10.00 g, 0.04483 mol), benzyl bromide (6.97 g, 0.0408 mol), potassium carbonate (11.26 g, 0.08147 mol) and butan-2-one (350 ml) was heated under reflux for 24 hrs. (GLC and TLC analyses revealed a complete reaction). The potassium carbonate was filtered off and the filtrate was washed with water before being dried (MgSO4). The drying agent was filtered off and the solvent was removed in vacuo to give a pale orange solid. The crude product was crystallized twice from ethanol and was dried in vacuo (P2O5, CaCl2, paraffin wax, 48 h) to afford white crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hrs
  3. customa complete reaction)
  4. filtrationThe potassium carbonate was filtered off
  5. washthe filtrate was washed with water
  6. dry with materialbefore being dried (MgSO4)
  7. filtrationThe drying agent was filtered off
  8. customthe solvent was removed in vacuo
  9. customto give a pale orange solid
  10. customThe crude product was crystallized twice from ethanol
  11. dry with materialwas dried in vacuo (P2O5, CaCl2, paraffin wax, 48 h)
  12. customto afford white crystals

Sources & evidence

ORD record
ord-fed0d437a9b24cdabb8fb918b93295e8
Source dataset
uspto-grants-2004_12
Patent number
US06830789B2

Reaction notes

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