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

HRID 328794Notes

Reaction equation

HRID 328794 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 evaportor 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) δ 1.4-2.2 (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 evaportor
  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-f3bca2b712d24ae19f40d00570aed0bd
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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