Chlorotrimethylsilane → (2-Chloro-6-fluoro-3-methoxyphenyl)trimethylsilane

HRID 1172824Notes

Reaction equation

HRID 1172824 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Li]C(C)(C)C.CCCCC.[CH3:21][Si:22]([CH3:25])([CH3:24])Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([Cl:1])[C:7]=1[Si:22]([CH3:25])([CH3:24])[CH3:21]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8003PentaneHCID 516892Sodium BicarbonateHCID 27735802-Chloro-4-fluoroanisoleHCID 178418306HCID 178418306, compound

Product 1

HCID 46941339(2-Chloro-6-fluoro-3-methoxyphenyl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-fluoroanisole (16.5 g, 100 mmol) in THF (500 mL) cooled at −75° C. was added dropwise a solution of t-BuLi in pentane (1.7 M, 61.8 mL, 105 mmol). The reaction was kept at −75° C. for 15 min, quenched at −75° C. with trimethylchlorosilane (19.0 mL, 150 mmol) and finally poured into a saturated solution of sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel eluting with 20:1 hexane:diethyl ether to give the title product.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel eluting with 20:1 hexane

Sources & evidence

ORD record
ord-cbd6a7b66c6640aebfde53b5897cfb8c
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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