1-Butyne → 1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene

HRID 423179

反応式

HRID 423179 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12].[CH:13]#[C:14][CH2:15][CH3:16]>C(NCC)C.CCOCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12])#[C:14][CH2:15][CH3:16]

参加物

7

反応物 2

HCID 78461-ButyneHCID 108236251-Bromo-4-fluoro-2-(methoxymethoxy)benzene

生成物 1

HCID 595651761-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene収率 91%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 8021Diethylamine溶媒

反応条件

温度
70 °C

実験手順

1-Bromo-4-fluoro-2-methoxymethoxy-benzene (7.6 g, 32 mmol) is placed in a pressure flask, dissolved in diethylamine (65 mL) and degassed with nitrogen for 15 min. An excess of butyne is bubbled through the solution, CuI (1.9 g, 10 mmol) and PdCl2(PPh3)2 (2.3 g, 3.3 mmol) are added, and the flask is heated to 70° C. for 44 h. The mixture is diluted with ether, then washed with saturated aqueous NH4Cl and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane) to provide 6.12 g (91%) of the title compound as an orange solid. GCMS m/e 208 [M]+.

後処理

  1. customdegassed with nitrogen for 15 min
  2. additionare added
  3. washwashed with saturated aqueous NH4Cl and brine
  4. dry with materialThe organic portion is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane)

出典と根拠

ORDレコード
ord-bc3a652c23944c49801cf9ef32298cc6
出典データセット
uspto-grants-2012_01
特許番号
US08101761B2

関連ノート

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