4-Fluorophenol → 1-[(But-3-yn-1-yl)oxy]-4-fluorobenzene

HRID 562654Notes

Reaction equation

HRID 562654 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](O)[CH2:10][C:11]#[CH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][C:10]#[CH:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 222797471-[(But-3-yn-1-yl)oxy]-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluorophenol (5.00 g, 44.6 mmol), 3-butyn-1-ol (3.38 ml, 44.6 mmol) and triphenylphosphine (17.5 g, 66.9 mmol) in tetrahydrofuran (100 ml) was added diethyl azodicarboxylate (11.7 g, 66.9 mmol) with stirring under ice-cooling, and then the resulting mixture was stirred at room temperature for 18 hours. After stirring, the reaction mixture was evaporated in vacuo, and to the residue were added hexane (200 ml) and ethyl acetate (20 ml). The precipitate separated out was filtered off, and the filtrate was evaporated in vacuo. The residue obtained was purified by flash chromatography on a silica gel column using hexane as the eluent to afford the title compound.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 18 hours
  3. stirringAfter stirring
  4. customthe reaction mixture was evaporated in vacuo
  5. additionto the residue were added hexane (200 ml) and ethyl acetate (20 ml)
  6. customThe precipitate separated out
  7. filtrationwas filtered off
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue obtained
  10. customwas purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-cc5e11e48e4a4c729a8b7daf12c6afe0
Source dataset
uspto-grants-2011_11
Patent number
US08067396B2

Reaction notes

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