Chlorotrimethylsilane → HCID 67955212, compound

HRID 1803648Notes

Reaction equation

HRID 1803648 reaction equation
[Li]CC[CH2:4][CH3:5].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].O1[CH2:18][CH2:17]CC1.C[Si:20](Cl)([CH3:22])C.[C:24](OC)(C)(C)C>O>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:20]([CH2:4][CH3:5])([CH2:17][CH3:18])[CH2:22][CH3:24])[C:8]=1[F:13]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 97061,2-DifluorobenzeneHCID 15413tert-Butyl methyl etherHCID 178418339Butyllithium

Product 1

HCID 67955212HCID 67955212, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

625 ml (1 mol) of 1.6 M BuLi are added dropwise at −78° C. to a solution of 114 g (1 ml) of 1,2-difluorobenzene in 11 of dry tetrahydrofuran. After 1 hour, 140 ml (120 g, 1.1 mol) of trimethylsilyl chloride are slowly added dropwise at −78° C. The mixture is allowed to warm to room temperature overnight, and then 200 ml of methyl ter-butyl ether and 200 ml of water are added. The organic phase is washed with water (2×100 ml) and sat. NaCl (1×100 ml) and dried using magnesium sulfate, and the solvent is removed under reduced pressure. 170 g (91%) of 5 distil over from the residue at from 100 to 102° C./70 mbar.

Workup

  1. washThe organic phase is washed with water (2×100 ml) and sat. NaCl (1×100 ml)
  2. customdried
  3. customthe solvent is removed under reduced pressure
  4. custom170 g (91%) of 5 distil over from the residue at from 100 to 102° C./70 mbar

Sources & evidence

ORD record
ord-7dc5faf8fffa457bbb6562012632b700
Source dataset
uspto-grants-2013_01
Patent number
US08350100B2

Reaction notes

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