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

HRID 1063468Notes

Reaction equation

HRID 1063468 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

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) were dissolved in tetrahydrofuran (100 ml), and diethyl azodicarboxylate (11.7 g, 66.9 mmol) was added thereto in an ice bath followed by stirring for 18 hours at room temperature. After the solvent was concentrated in vacuo, hexane (200 ml) and ethyl acetate (20 ml) were added thereto, and the resulting precipitate was filtered out, and then the filtrate was concentrated in vacuo. The obtained residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:0) to afford the title compound.

Workup

  1. customin an ice bath followed
  2. concentrationAfter the solvent was concentrated in vacuo, hexane (200 ml) and ethyl acetate (20 ml)
  3. additionwere added
  4. filtrationthe resulting precipitate was filtered out
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe obtained residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=1:0)

Sources & evidence

ORD record
ord-1a30c9090ada4d78a0031d38156ba815
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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