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

HRID 842034
ノート
印刷プレビュー

反応式

HRID 842034 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 136722741-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene収率 103.7%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09222142c3d644fd9fcc3645085f1806
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06372754B1

反応ノート

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