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

HRID 912511Notes

Reaction equation

HRID 912511 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-35316238b9c6450ea84fb7cf893a78e4
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

Loading…