2-Methoxyethanol → HCID 66654962, compound

HRID 879104Notes

Reaction equation

HRID 879104 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:10][O:11][CH2:12][CH2:13]O.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>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([O:9][CH2:13][CH2:12][O:11][CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 759283,5-DifluorophenolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 66654962HCID 66654962, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-difluorophenol (1.0 equiv.), 2-methoxyethanol (3.0 equiv.) and triphenylphosphine (3.0 equiv) in THF (0.1 M) was added DIAD (3.0 equiv.). After stirring at rt for 18 hours, the volatiles were removed in vacuo and the residue was purified by SiO2 chromatography to yield 1,3-difluoro-5-(2-methoxyethoxy)benzene in 95% yield. 1H NMR (400 MHz, <cdcl3>) δ ppm 6.41-6.47 m (3H), 4.08 (t, 2H), 3.74 (t, 2H), 3.45 (s, 3H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-69fbaf677c624988824ad664caad4934
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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