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

HRID 1515435ノート

反応式

HRID 1515435 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 109800492-(T-Butyldimethylsilyloxy)-4-bromoanisole収率 100%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7402ff6a063a47c7849dd24c2d3f8809
出典データセット
uspto-grants-2012_07
特許番号
US08222424B2

反応ノート

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