Water → tert-Butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane

HRID 1047479Notes

Reaction equation

HRID 1047479 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:13]=2[F:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[H-].[Na+].O>CN(C=O)C.C(OCC)(=O)C>[C:28]([Si:25]([O:24][CH2:23][CH2:22][CH:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[C:12]1[C:13]([F:20])=[CH:14][CH:15]=[C:16]([F:19])[C:17]=1[F:18])([CH3:27])[CH3:26])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 589503342-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene

Product 1

HCID 58950531tert-Butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene (4.0 g, 12.5 mmol) was dissolved in 40 mL dry DMF. (2-Bromo-ethoxy)-tert-butyl-dimethylsilane (4.1 g, 17.1 mmol) and NaH (2.28 g, 95.0 mmol) were added respectively. The solution was stirred at room temperature overnight. 200 mL of water and 200 mL of EtOAc were added. The aqueous layer was washed with 100 mL of EtOAc. The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was purified using column chromatography (hex./EtOAc 100/0 to 90/10 in 45 min, 1.7 g, 28%). 1H NMR (CDCl3 400 MHz) δ 7.65 (m, 2H), 7.46 (m, 2H), 7.14 (m, 1H), 6.84 (m, 0.5), 6.73 (m, 0.5H), 4.87 (m, 1H), 4.79 (m, 1H), 4.37 (m, 1H), 2.55 (m, 2H), 2.04 (s, 9H), −0.13 (d, J=22.7 Hz, 6H).

Workup

  1. washThe aqueous layer was washed with 100 mL of EtOAc
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified
  6. customcolumn chromatography (hex./EtOAc 100/0 to 90/10 in 45 min, 1.7 g, 28%)

Sources & evidence

ORD record
ord-2fb5a3bd23264375adc4c7c38583eba8
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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