Triethylamine → [(3-Bromophenyl)methoxy](tert-butyl)diphenylsilane

HRID 1648681Notes

Reaction equation

HRID 1648681 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:6]([CH2:5][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][CH:7]=1)[Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 851413-Bromobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 14903623[(3-Bromophenyl)methoxy](tert-butyl)diphenylsilaneYield 111.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-bromobenzyl alcohol (21) (10.0 g, 53.5 mmol), 4-dimethylaminopyridine (0.33 g, 2.7 mmol), and t-butylchlorodiphenylsilane (17.6 g, 64.2 mmol) in anhydrous CH2Cl2 (240 mL) was cooled to 0° C. under argon. Triethylamine (8.1 g, 80.2 mmol) was added dropwise via syringe and the reaction mixture was allowed to warm to room temperature over 3.5 h. The reaction solution was washed with water, and the aqueous portion was extracted again with CH2Cl2. The organic layers were combined, washed sequentially with 1N HCI solution, water, and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 25.3 g of 22 as a clear, pale yellow oil. Purification by column chromatography (20:1 ratio silica gel/crude product; elution with 5% to 7.5% ethyl acetate/hexanes) yielded 21.2 g (93%) of 22 as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ7.63-7.65 (m, 4H, ArH), 7.35-7.48 (m, 8 H, ArH), 7.18-7.28 (m, 2H, ArH), 4.72 (s, 2H, CH2OSi), and 1.05 (s, 9H, SiC(CH3)3).

Workup

  1. washThe reaction solution was washed with water
  2. extractionthe aqueous portion was extracted again with CH2Cl2
  3. washwashed sequentially with 1N HCI solution, water, and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ade28e844cc5477ea2b807cd414354f8
Source dataset
uspto-grants-1995_07
Patent number
US05436369

Reaction notes

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