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

HRID 842034Notes

Reaction equation

HRID 842034 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-09222142c3d644fd9fcc3645085f1806
Source dataset
uspto-grants-2002_04
Patent number
US06372754B1

Reaction notes

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