Triphenylphosphine → 4-Fluoro-2-bromophenol methylcyclopropyl ether

HRID 930908Notes

Reaction equation

HRID 930908 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH:10]1([CH2:13]O)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:13][CH:10]1[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 6054722-Bromo-4-fluorophenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 435603964-Fluoro-2-bromophenol methylcyclopropyl etherYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-4-fluorophenol (0.50 g, 2.6 mmol) in tetrahydrofuran (13 mL) were added cyclopropanemethanol (0.209 mL, 2.62 mmol), triphenylphosphine (0.687 g, 2.62 mmol), and DIAD (0.509 mL, 2.62 mmol). The reaction mixture was stirred for 16 hours at ambient temperature. The solvent was removed under reduced pressure. The residue was triturated with hexanes. The mixture was filtered, and the filtrate containing the product was concentrated by under reduced pressure. The residue was purified by flash chromatography (silica gel, hexanes) to provide the title compound (400 mg, 62% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with hexanes
  3. filtrationThe mixture was filtered
  4. additionthe filtrate containing the product
  5. concentrationwas concentrated by under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, hexanes)

Sources & evidence

ORD record
ord-fd88caf358cc4098b9e9ed69568309f2
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

Loading…