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

HRID 84426

반응식

HRID 84426 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca22d59813074d9f89ca12f80f9459cc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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