Triphenylphosphine → 3-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

HRID 84426

反応式

HRID 84426 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][S:11][CH:12]=1)[C:5]#[N:6]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 753413-Bromo-4-hydroxybenzonitrileHCID 83731Thiophene-3-ethanolHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 568341533-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-bromo-4-hydroxybenzonitrile (15.0 g) in THF (100 mL) was added 2-(3-thienyl)ethanol (7.94 mL) and triphenyl phosphine (19.84 g). The reaction was cooled to 0° C. and diethylazodicarboxylate (11.92 mL) was added dropwise. The reaction was stirred at room temperature for 16 h. The solvent was then reduced in vacuo and the residue redissolved in diethyl ether (100 mL). The mixture was stirred at 0° C. for 10 min and then filtered. The filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 3-bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile.

後処理

  1. stirringThe mixture was stirred at 0° C. for 10 min
  2. filtrationfiltered
  3. washThe filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified on silica

出典と根拠

ORDレコード
ord-ca22d59813074d9f89ca12f80f9459cc
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

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