Chlorotrimethylsilane → 1,2-Difluoro-3-trimethylsilylbenzene

HRID 351353

Reaction equation

HRID 351353 reaction equation
[Li]CCCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[CH3:14][Si:15](Cl)([CH3:17])[CH3:16].C(OC)(C)(C)C>O1CCCC1.O>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:15]([CH3:17])([CH3:16])[CH3:14])[C:8]=1[F:13]

Participants

7

Reactant 4

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

Product 1

HCID 108993711,2-Difluoro-3-trimethylsilylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

625 ml (1 mol) of 1.6 M BuLi are added dropwise at −78° C. to a solution of 114 g (1 mol) of 1,2-difluorobenzene in 1 l 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 tert-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-5b4a85235cc44b289503edb92ef623ce
Source dataset
uspto-grants-2007_02
Patent number
US07183447B2

Linked notes

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