Water → 2-Bromo-7-(methylsulfanyl)naphthalene

HRID 2238428Notes

Reaction equation

HRID 2238428 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6](Br)=[CH:7][CH:8]=2)[CH:3]=1.[Li]CCCC.[CH3:18][S:19]SC.O>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([S:19][CH3:18])=[CH:7][CH:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 6253552,7-DibromonaphthaleneHCID 178418339Butyllithium

Product 1

HCID 445509852-Bromo-7-(methylsulfanyl)naphthaleneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A stirred solution of 189 (5.72 g, 20.0 mmol) in THF (80 mL) was treated dropwise at −78° C. with n-BuLi (2.5 M in hexanes, 8.40 mL, 21.0 mmol) under N2. The mixture was stirred at −78° C. for 20 min, then treated slowly with dimethyl disulfide (2.16 mL, 24 mmol) and allowed to warm to room temperature. The solvent was removed under reduced pressure to give a residue that was shaken with water, and the resulting solid was crystallised fom petroleum ether to give 2-bromo-7-(methylsulfanyl)naphthalene (199) (4.14 g, 82%): mp 80-81° C.; 1H NMR [(CD3)2SO] δ 8.11 (d, J=1.9 Hz, 1H), 7.86 (d, J=9.1 Hz, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.71 (d, J=1.8 Hz, 1H), 7.54 (dd, J=8.72, 2.0 Hz, 1H), 7.44 (dd, J=8.6, 2.0 Hz, 1H), 2.58 (s, 3H). Anal. (C11H9BrS) C, H, S.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue that
  4. customthe resulting solid was crystallised fom petroleum ether

Sources & evidence

ORD record
ord-538133da078045c08f1833bb9cc5c53a
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…