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2-Bromoethanol → 1-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene

HRID 842034
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HRID 842034 반응식
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Br:13][CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CCCCCC>[Br:13][CH2:14][CH2:15][O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 70015p-(Trifluoromethoxy)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 136722741-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene수율 103.7%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매

실험 절차

4-(Trifluoromethoxy)phenol (15 g), 2-bromoethanol (7.76 g) and triphenylphosphine (22.1 g) were dissolved in tetrahydrofuran (250 ml). Diethyl azodicarboxylate (13.3 ml) was added dropwise to the stirred mixture and stirring was continued for 12 hours. The mixture was concentrated in vacuo to give a yellow oil. The oil was diluted with hexane to precipitate the triphenylphosphine oxide by-product which was removed by filtration. The filtrate was concentrated and purified on silica using 10% ether in hexane as eluant to give the product (18.35 g). 1H NMR (250 MHz, CDCl3) δ 3.63 (2H, t, J 6.1 Hz), 4.30 (2H, t, J 6.2 Hz), 6.84-6.95 (2H, m), 7.12-7.17 (2H, m).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a yellow oil
  3. customto precipitate the triphenylphosphine oxide by-product which
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated
  6. custompurified on silica using 10% ether in hexane as eluant

출처 및 근거

ORD 기록
ord-09222142c3d644fd9fcc3645085f1806
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06372754B1

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