tert-Butyldimethylsilyl chloride → Tert-butyl(dimethyl)-{[3-nitro-5-(trifluoromethyl)benzyl]oxy}silane

HRID 1640156Notes

Reaction equation

HRID 1640156 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(Cl)Cl>[C:28]([Si:25]([CH3:27])([CH3:26])[O:15][CH2:14][C:6]1[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 58902383Tert-butyl(dimethyl)-{[3-nitro-5-(trifluoromethyl)benzyl]oxy}silaneYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (2.80 g, 12.7 mmol) in DCM (20 mL) was added DIPEA (6.62 mL, 38.00 mmol). The reaction mixture was cooled to 0° C. tert-Butyldimethylsilyl chloride (3.82 g, 25.3 mmol) was added dropwise and the reaction mixture was allowed to stir at rt over the weekend. The reaction mixture was diluted with DCM and washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl(dimethyl)-{[3-nitro-5-(trifluoromethyl)benzyl]oxy}silane (3.71 g, 87%) as a white solid. 1H NMR (400 MHz,CDCl3, HCl salt) δ: 8.35-8.41 (m, 2H), 7.92 (s, 1H), 4.88 (s, 2H), 0.97 (s, 9H), and 0.15 (s, 6H).

Workup

  1. additionwas added dropwise
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-296d8425555d467381585f5fa9e4f1cd
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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