4-Ethoxy-2-fluoro-1-(phenylmethoxy)benzene → 4-Ethoxy-2-fluorophenol

HRID 1931569Notes

Reaction equation

HRID 1931569 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][C:10]=1[F:18])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:18])[CH:11]=1)[CH3:17]

Participants

4

Reactant 1

HCID 669153164-Ethoxy-2-fluoro-1-(phenylmethoxy)benzene

Product 1

HCID 180033714-Ethoxy-2-fluorophenolYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium-on-carbon (26 mg, 0.11 mmol) was added to a solution of 1-benzyloxy-4-ethoxy-2-fluoro-benzene (260 mg, 1.06 mmol) in ethyl acetate (20 mL). The reaction mixture was shaken under hydrogen (30 psi) overnight. The reaction mixture was filtered through celite and a pad of silica gel, which was washed with 40% ethyl acetate/hexane. The solvent was removed to give 4-ethoxy-2-fluoro-phenol (155 mg, 94%) as a white solid which was used directly in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 1.25 (t, 3H, J=6.9 Hz), 3.89 (q, 2H, J=6.9 Hz), 6.52-6.56 (m, 1H), 6.71-6.85 (m, 2H), 9.21 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washa pad of silica gel, which was washed with 40% ethyl acetate/hexane
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-2e96ac1afa9f47778b20056c1688ba18
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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