Sodium Hydroxide → 2-(4-Fluorophenylmethoxymethyl)thiophene

HRID 52185

Reaction equation

HRID 52185 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][OH:16].[OH-].[Na+]>CS(C)=O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.[Cl-].[Na+].O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:16][CH2:15][C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 694672-Thiophenemethanol

Product 1

HCID 199633152-(4-Fluorophenylmethoxymethyl)thiopheneYield 86%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution in DMSO (30 mL) of 4-fluorobenzyl bromide (3.27 mL, 26.3 mmol), 2-thiophenemethanol (3.00 mL, 31.7 mmol), and benzyltrimethylammonium chloride (244 mg, 1.31 mmol) was added NaOH (6.31 g, 159 mmol) and the reaction mixture was stirred for 17 hours at ambient temperature. The reaction mixture was poured into brine and extracted with ether. The organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (20% ethyl acetate/hexane) gave 2-(4-fluorophenylmethoxymethyl)thiophene (5.03 g, 86% ).

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with 1N aqueous H3PO4 (3×), H2O (3×), saturated aqueous NaHCO3 (2×), and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7211a6dbcfe0433eae7be03d10f925a4
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Linked notes

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