Diethyl Ether → tert-Butyl-(3-chloromethylsulfanyl-phenoxy)-dimethyl-silane

HRID 1685666

Reaction equation

HRID 1685666 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][C:18]1[CH:19]=[C:20]([SH:24])[CH:21]=[CH:22][CH:23]=1)([CH3:15])([CH3:14])[CH3:13].CCOCC.OS([O-])(=O)=O.[K+].Br[CH2:39][Cl:40]>>[C:12]([Si:16]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH2:39][Cl:40])[CH:19]=1)([CH3:26])[CH3:25])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6333BromochloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 219768683-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenethiol

Product 1

HCID 58734012tert-Butyl-(3-chloromethylsulfanyl-phenoxy)-dimethyl-silane

Procedure

DBU (914 mg, 6.0 mmol) was added to a solution of 3-(tert-Butyl-dimethyl-silanyloxy)-benzenethiol (1.00 g, 4.16 mmol) in bromo-chloro methane (5 ml) at room temperature. Stirring was continued for 2 hours and Et2O (50 ml) and 2M KHSO4 (30 ml) were added. The organic layer was separated, washed with 2M KHSO4 (30 ml) and brine (30 ml), dried (Na2SO4) and concentrated under reduced pressure. The resulting oil was analysed by 1H-NMR spectroscopy and was used without further purification. Yield: 1.01 g (84%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 2M KHSO4 (30 ml) and brine (30 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customwas used without further purification

Sources & evidence

ORD record
ord-1507da1f180a4e8ea82054e9c26f141d
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Linked notes

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