1,2-Dibromoethane → HCID 22131449, compound

HRID 860856Notes

Reaction equation

HRID 860856 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.[Br:13][CH2:14][CH2:15]Br.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:15][CH2:14][Br:13])[CH:8]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 22131449HCID 22131449, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A round-bottom flask containing 1.0 g (4.5 mmol) of 6-bromo-2-naphthol, 1,2-dibromoethane (135 mmol, 12 mL), potassium hydroxide (5 mL of a 40% solution) and tetrabutylammonium bromide (1.35 mmol, 0.43 g) was heated at 100° C. for 3 h. The reaction mixture was diluted with 150 mL of CH2Cl2 and washed with water and brine, dried over sodium sulfate and concentrated under vacuum to give the desired compound in 100% as a pale brown solid; 1HNMR (300 MHz, CDCl3) δ 3.70 (t, 2H), 4.40 (t, 2H), 7.05–7.90 (m, 6H). MS (DCI) m/z 330 (M+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-89df3958d02741a69222b100ca40dfd2
Source dataset
uspto-grants-2006_12
Patent number
US07153889B2

Reaction notes

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