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

HRID 1172824

반응식

HRID 1172824 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cbd6a7b66c6640aebfde53b5897cfb8c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834036B2

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