Water → 1-Fluoro-4-[[5-iodo-2-(phenylmethoxy)pentyl]oxy]benzene

HRID 1833480Notes

Reaction equation

HRID 1833480 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH:15]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(C1C=CC(C)=CC=1)(=O)=O.[I-:33].[Na+].O>CC(C)=O>[CH2:26]([O:25][CH:15]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH2:14][CH2:13][CH2:12][I:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 53816747HCID 53816747, compound

Product 1

HCID 213175661-Fluoro-4-[[5-iodo-2-(phenylmethoxy)pentyl]oxy]benzeneYield 79.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-benzyloxy-5-(4-fluorophenoxy)-1-pentanol tosylate (3.78 g., 8.24 mmoles) and sodium iodide (3.71 g., 25 mmoles) in acetone (70 ml.) is stirred at room temperature overnight (ca. 17 hours) and then heated on the steam bath for 15 minutes. The mixture is poured into cold water and extracted with ether three times. The combined extracts are washed with aqueous sodium thiosulfate and dried over anhydrous magnesium sulfate. The solvent is removed on a rotary evaporator to leave an oil residue which is further purified by chromatography on a silica gel (70 g.) column. Elution with chloroform gives the pure title compound (2.72 g., 6.57 mmoles, 79%). ir (neat) 3.28, 3.40, 6.20, 6.62, 6.87, 8.00, 8.23, 9.10, 12.07, 13.16, 13.58, 14.37μ; pmr (CCl4)δ1.4-2.2 (4H, m), 3.08 (2H, t, J=6Hz), 3.5-4.1 (3H, m), 4.47 (1H, d, J=12 Hz), 4.69 (1H, d, J=12Hz), 6.6-7.1 (4H, m), 7.20 (5H, s).

Workup

  1. temperatureheated on the steam bath for 15 minutes
  2. extractionextracted with ether three times
  3. washThe combined extracts are washed with aqueous sodium thiosulfate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent is removed on a rotary evaporator
  6. customto leave an oil residue which
  7. customis further purified by chromatography on a silica gel (70 g.) column
  8. washElution with chloroform

Sources & evidence

ORD record
ord-cfe5c938682248bf9babd60389920f53
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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