p-Toluenesulfonic acid monohydrate → 2-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethoxy)tetrahydro-2H-pyran

HRID 2079534Notes

Reaction equation

HRID 2079534 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[OH2:16].[C:17]1(C)C=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1>C1COCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][CH:21]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576575832-(4-Bromo-2-(trifluoromethyl)phenoxy)-ethanol

Product 1

HCID 576575782-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethoxy)tetrahydro-2H-pyranYield 2,164%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-(4-bromo-2-(trifluoromethyl)phenoxy)ethanol (16 g), 3,4-dihydro-2H-puran (9.5 g) and p-toluenesulfonic acid hydrate (0.5 g) in THF (100 ml) was stirred at room temperature for 1 hour then diluted with 5% sodium bicarbonate (300 ml) and extracted with ethyl acetate (500 ml). Organic layer was then dried over sodium sulphate, solvent removed under vacuum to give expected product (21 g).

Workup

  1. extractionextracted with ethyl acetate (500 ml)
  2. dry with materialOrganic layer was then dried over sodium sulphate, solvent
  3. customremoved under vacuum

Sources & evidence

ORD record
ord-4dacf220875849c0ab94082992f5d13f
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

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