Triethylamine → 2-(T-Butyldimethylsilyloxy)-4-bromoanisole

HRID 1515435노트

반응식

HRID 1515435 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:7]=1)[O:8][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1422285-Bromo-2-methoxyphenol

생성물 1

HCID 109800492-(T-Butyldimethylsilyloxy)-4-bromoanisole수율 100%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-bromo-2-methoxy-phenol (3.5 g, 17.2 mmol) dissolved in methylene chloride (50 mL) are added triethylamine (2.08 g, 20.6 mmol) and 4-dimethylaminopyridine (0.15 g, 0.86 mmol). Then tert-butyldimethylsilyl chloride is added slowly and the reaction mixture is stirred at room temperature for 16 h. The reaction is quenched with 10% of citric acid, and then the organic layer is washed with saturated sodium bicarbonate solution, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (15% ethyl acetate-hexane) provides 5.6 g (100%) of the title compound as a colorless oil. 1H NMR (CDCl3): δ 6.82 (m, 2H), 6.58 (d, J=9 Hz, 1H), 3.74 (s, 3H), 0.95 (s, 9H), 0.05 (s, 6H).

후처리

  1. customThe reaction is quenched with 10% of citric acid
  2. washthe organic layer is washed with saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (15% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-7402ff6a063a47c7849dd24c2d3f8809
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222424B2

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