Water → 4-Bromo-2-triisopropylsiloxynaphthalene

HRID 2369628Notes

Reaction equation

HRID 2369628 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([OH:14])[CH:5]=1.Cl[Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18].O>C1COCC1>[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([O:14][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 121155964-Bromo-2-naphthol

Product 1

HCID 671624644-Bromo-2-triisopropylsiloxynaphthaleneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.38 g, 15.9 mmol) was added portionwise to a solution of 4-bromo-2-naphthol (3.54 g, 15.9 mmol) in THF (50 mL) with stirring at 0° C. under N2. Ater 0.5 h chlorotriisopropylsilane (3.06 g, 15.9 mmol) was added dropwise at 0. The solution was stirred at room temperature for 2 h, poured into water (200 mL), extracted with DCM (dichloromethane) (4×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using hexanes as eluent. The solvent was removed under reduced pressure to give the title compound (5.78 g, 96%) as a colourless oil.

Workup

  1. stirringThe solution was stirred at room temperature for 2 h
  2. extractionextracted with DCM (dichloromethane) (4×50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9ffc7b4ec73c46d7b3c45d9187730492
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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