Chlorotrimethylsilane → (4-Chloro-2,6-difluorophenyl)trimethylsilane

HRID 1772867Notes

Reaction equation

HRID 1772867 reaction equation
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:9]([F:14])[CH:8]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 137000Benzene, 1-chloro-3,5-difluoro-HCID 178418339Butyllithium

Product 1

HCID 18935733(4-Chloro-2,6-difluorophenyl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added dropwise to a solution of 1-chloro-3,5-difluorobenzene (19.2 g, 0.13 mol) in THF (200 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of chlorotrimethylsilane (21.7 g, 0.2 mol) in THF (25 mL) was added dropwise. The reaction was allowed to warm to rt with stirring overnight before cooling and quenching with H2O. The phases were separated and pentane (200 mL) was added; after washing with H2O the solution was dried over MgSO4 and carefully concentrated in vacuo to yield the title compound as a solution in THF (46 g) which was in the next step without further purification.

Workup

  1. additionAfter the addition
  2. additionwas added dropwise
  3. temperatureto warm to rt
  4. temperaturebefore cooling
  5. customquenching with H2O
  6. customThe phases were separated
  7. additionpentane (200 mL) was added
  8. washafter washing with H2O the solution
  9. dry with materialwas dried over MgSO4
  10. concentrationcarefully concentrated in vacuo

Sources & evidence

ORD record
ord-6d3fd43fc00d4eeca191889ae9abdcfd
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

Loading…