p-Toluenesulfonic acid monohydrate → 2-(3-(4-bromo-2-(trifluoromethyl)phenoxy)propoxy)tetrahydro-2H-pyran

HRID 912499Notes

Reaction equation

HRID 912499 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[OH2:17].[C:18]1(C)C=[CH:22][C:21](S(O)(=O)=O)=[CH:20][CH:19]=1>C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][O:10][CH:22]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:4]([C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576575913-(4-Bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol

Product 1

HCID 576575642-(3-(4-bromo-2-(trifluoromethyl)phenoxy)propoxy)tetrahydro-2H-pyranYield 979.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 3-(4-bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol (12 g), 3,4-dihydro-2H-puran (6.75 g) and p-toluenesulfonic acid hydrate (0.76 g) in THF (100 ml) was stirred at room temperature for 1 hour then diluted with 10% sodium carbonate (50 ml) and extracted with ethyl acetate (2×150 ml). Organic layer was then dried over sodium sulphate, solvent removed under reduced pressure to give expected product (15 g). 1H NMR (CDCl3) δ: 7.67 (d, 1H), 7.56 (dd, 1H), 6.90 (dd, 1H), 4.56 (dd, 1H), 4.15 (t, 2H), 3.75-4.0 (m, 2H), 3.4-3.65 (m, 2H), 2.10 (m, 2H), 1.4-2.0 (m, 6H).

Workup

  1. extractionextracted with ethyl acetate (2×150 ml)
  2. dry with materialOrganic layer was then dried over sodium sulphate, solvent
  3. customremoved under reduced pressure

Sources & evidence

ORD record
ord-df170658059a41dab3eeed35db8907c1
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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