Hydrogen Bromide → 1-(2-Bromoethyl)naphthalene

HRID 370648Notes

Reaction equation

HRID 370648 reaction equation
[BrH:1].O[CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O>[Br:1][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13047Naphthalen-1-ethanol

Product 1

HCID 1395411-(2-Bromoethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of hydrobromic acid (50 ml, 46% w/v) and 1-(2-hydroxyethyl)naphthalene (10.0 g, 0.058 mol) was stirred and heated under reflux for 4 h. After cooling, the reaction mixture was diluted with water (150 ml), and the resulting precipitate was extracted with ether (3×150 ml). The ether extracts were combined and dried (MgSO4), when the ether was evaporated under reduced pressure, to afford 1-(2-bromoethyl)-naphthalene which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. extractionthe resulting precipitate was extracted with ether (3×150 ml)
  5. dry with materialdried (MgSO4), when the ether
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-9bcca1b5b5c04a4da3b02ed9fb09e4a5
Source dataset
uspto-grants-1985_07
Patent number
US04528195

Reaction notes

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