Chlorotrimethylsilane → 1,2-Difluoro-3-trimethylsilylbenzene

HRID 1645455Notes

Reaction equation

HRID 1645455 reaction equation
[Li]CCCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].O1CCCC1.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>O.C(OC)(C)(C)C>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:20]([CH3:22])([CH3:21])[CH3:19])[C:8]=1[F:13]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 97061,2-DifluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 108993711,2-Difluoro-3-trimethylsilylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

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 I 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-7767ed041c2d452caf9fddc73b12f060
Source dataset
uspto-grants-2012_02
Patent number
US08124817B2

Reaction notes

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