Triethylamine → 2-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

HRID 2212568Notes

Reaction equation

HRID 2212568 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.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 134730832-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthaleneYield 95%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-bromo-naphthalen-2-ol (18.0 g, 80.7 mmol), t-butyldimethylsilyl chloride (14.6 g, 96.8 mmol), triethyl amine (12.3 g, 121.0 mmol), and DMAP (0.75 g) in THF (400 mL) was stirred at room temperature overnight. The reaction was taken up in ethyl acetate and washed with 1N HCl (2×) and brine, dried over magnesium sulfate, and concentrated to give an oil. The product was crystallized from acetonitrile cooled to 0° C. to give (6-Bromo-naphthalen-2-yloxy)-tert-butyl-dimethyl-silane (25.8 g, 95%) as an off-white solid.

Workup

  1. washwashed with 1N HCl (2×) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give an oil
  5. customThe product was crystallized from acetonitrile

Sources & evidence

ORD record
ord-d6e44e6205e54a79b23687bf5e818d56
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

Loading…