2-Bromoanisole → HCID 11558102, 화합물

HRID 1107083노트

반응식

HRID 1107083 반응식
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[CH3:15][Sn:16](Cl)([CH3:18])[CH3:17]>C(OCC)C>[CH3:15][Sn:16]([CH3:18])([CH3:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

참가 물질

5

반응물 3

HCID 113582-BromoanisoleHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

생성물 1

HCID 11558102HCID 11558102, 화합물수율 76.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a stirring solution of n-BuLi (2.6 mL, 2.5M in hexane, 6.42 mmol) in diethyl ether (2.5 mL) at -78° C. was added 2-bromoanisole (1.0 g, 5.35 mmol) in diethyl ether (2 mL) dropwise. After stirring for 1h at -78° C., trimethyltin chloride (6.4 mL, 1.0M in THF, 6.42 mmol) was added dropwise. The mixture was allowed to stir an additional 2h while slowly warming to room temperature. The mixture was then washed with saturated aqueous NaHCO3. The aqueous layer was extracted with diethyl ether (1×50 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (silica gel, hexane) to yield the title compound as a colorless oil (1.11 g, 76%). 1HNMR (400 MHz, CDCl3) δ7.47 (d, 1H), 7.40 (t, 1H), 7.05 (t, 1H), 6.90 (d, 1H), 3.36 (s, 3H), 0.34 (s, 9H).

후처리

  1. washThe mixture was then washed with saturated aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with diethyl ether (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, hexane)

출처 및 근거

ORD 기록
ord-979b4a2c437f43bfaf62d715044ebc22
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057362

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