Water → (4-Bromo-2-methyl-benzyloxy)-trimethylsilane

HRID 1935933Notes

Reaction equation

HRID 1935933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.C(N(CC)CC)C.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 22280088(4-Bromo-2-methylphenyl)methanol2×

Product 1

HCID 22568853(4-Bromo-2-methyl-benzyloxy)-trimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (4-bromo-2-methyl-phenyl)-methanol (Intermediate 133, 500.0 mg, 2.48 mmols), in 10 mL THF was added triethylamine (374.0 mg, 3.70 mmols) and chlorotrimethylsilane (297.0 mg, 2.70 mmols). The resulting solution was stirred for 17 hours at 25° C. and then treated with H2O and extracted with Et2O. The combined organic layers were washed with H2O, 10% aqueous HCl, saturated NaHCO3, and saturated NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 550.0 mg (81%), was isolated by column chromatography (5% EtOAc-hexanes) as a colorless oil.

Workup

  1. extractionextracted with Et2O
  2. washThe combined organic layers were washed with H2O, 10% aqueous HCl, saturated NaHCO3, and saturated NaCl
  3. dry with materialbefore being dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57452bf7f41f4f67b3b560ac327edb73
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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