4-Bromobenzyl alcohol → (4-Bromo-benzyloxy)-triisopropyl-silane

HRID 1161023Notes

Reaction equation

HRID 1161023 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[CH:21]([Si:24](Cl)([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:24]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 701194-Bromobenzyl alcoholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139400Triisopropylsilyl chloride

Product 1

HCID 11439315(4-Bromo-benzyloxy)-triisopropyl-silaneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a solution of 4-bromobenzyl alcohol (50 g, 267.3 mmol), DBU (48 ml, 320.8 mmol) and dichloromethane (600 mL) in an ice/water bath. Add triisopropylsilylchloride (63 mL, 294 mmol) over 10 min via an addition funnel and stir the reaction mixture for 20 hours at room temperature. Wash the mixture with water (2×600 mL), dry over anhydrous magnesium sulfate, filter and concentrate. Purify the residue via silica chromatography eluting with 9:1 hexanes:ethyl acetate to give the title compound (91.5 g, 99%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.47-7.50 (m, 2H), 7.28-7.30 (m, 2H), 4.81 (s, 1.11-1.24 (m, 21H).

Workup

  1. washWash the mixture with water (2×600 mL)
  2. dry with materialdry over anhydrous magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue via silica chromatography
  6. washeluting with 9:1 hexanes

Sources & evidence

ORD record
ord-bb38c921a7044cfaae42a137ac2955be
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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