Triphenylphosphine → 1-(1-Trifluoromethylprop-1-en-3-yloxy)-2-bromo-4-fluorobenzene

HRID 1815802

Reaction equation

HRID 1815802 reaction equation
[F:1][C:2]([F:8])([F:7])[CH:3]=[CH:4][CH2:5][OH:6].[Br:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[F:1][C:2]([F:8])([F:7])[CH:3]=[CH:4][CH2:5][O:6][C:11]1[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[Br:9]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6054722-Bromo-4-fluorophenolHCID 27770764,4,4-Trifluoro-2-buten-1-ol

Product 1

HCID 539219781-(1-Trifluoromethylprop-1-en-3-yloxy)-2-bromo-4-fluorobenzeneYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.10 gm (16.7 mMol) 1-trifluoromethylprop-1-en-3-ol, 3.19 gm (16.7 mMol) 2-bromo-4-fluorophenol, and 4.81 gm (18.4 mMol) triphenylphosphine in 25 mL dichloromethane was cooled to 0° C. and then 2.9 mL (18.4 mMol) diethyl azodicarboxylate were added. The reaction mixture was stirred for 1 hour at room temperature and then the reaction mixture was directly subjected to flash silica gel chromatography, eluting with 20:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 6 gm of crude 1-(1-trifluoromethylprop-1-en-3-yloxy)-2-bromo-4-fluorobenzene.

Workup

  1. washeluting with 20:1 hexane
  2. additionFractions containing product
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abfd6120e19141a8b130608e42b5b89d
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Linked notes

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