Propargyl alcohol → 3-(3-Amino-4-Nitrophenyl)-2-propyn-1-ol

HRID 252813ノート

反応式

HRID 252813 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH2:12]([OH:15])[C:13]#[CH:14]>COCCOC.C(N(CC)CC)C.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[NH2:8][C:6]1[CH:7]=[C:2]([C:14]#[C:13][CH2:12][OH:15])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

参加物

8

反応物 2

HCID 7859Propargyl alcoholHCID 53147665-Bromo-2-nitroaniline

生成物 1

HCID 597369853-(3-Amino-4-Nitrophenyl)-2-propyn-1-ol収率 83%

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8471Triethylamine溶媒

実験手順

A suspension of bromoarene 2 (447 mg g; 2.06 mmol); tetrakis(triphenylphosphine) palladium(0) (145 mg, 0.12 mmol) and copper(I)iodide (143 mg, 0.75 mmol) in degassed ethyleneglycol dimethylether (2.5 mL) and triethylamine (1.5 mL), was stirred at room temperature under nitrogen in the dark for 10 min and then treated with neat prop-2-yn-1-ol (0.7 mL, 12 mmol) (or any other alkyne of choice, 5 eq.), and the mixture stirred under the same conditions for 48 h, diluted with dichloromethane (50 mL), filtered through a celite pad and concentrated. Purification by flash chromatography (eluent 50 to 75% AcOEt in hexane) afforded compound 72 (328 mg, 83% yield).

後処理

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated
  3. customPurification by flash chromatography (eluent 50 to 75% AcOEt in hexane)

出典と根拠

ORDレコード
ord-00ed007235bd4f8d9c3b37583f62e169
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

反応ノート

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