Sodium Chloride → 2-(2'-Bromo-4-fluorophenoxy)tetrahydro-2H-pyran

HRID 13638

Reaction equation

HRID 13638 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Br:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[OH:32].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>ClCCl.O>[Br:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[O:32][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 593402472-(2'-Bromo-4-fluorophenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 478.0 ml (5.24 mol) of 3,4-dihydropyran and 750 ml of dichloromethane was admixed with 65.4 g (260 mmol) of pyridinium p-toluenesulfonate. Subsequently, a solution of 500.0 g (2.62 mmol) of 2-bromo-4-fluorophenol in 500 ml of dichloromethane was added dropwise. After stirring for 24 h, the reaction mixture was admixed with a solution of 50 g of potassium carbonate in 500 ml of water, and then with 500 ml of saturated sodium chloride solution. The organic phase was removed, dried over potassium carbonate and, after freeing it of the solvent and potassium carbonate, fractionally distilled (approx. 1 mbar, top temperature from 79 to 82° C.) by means of a Vigreux column (40 cm). The product was obtained as a colorless, low-viscosity oil. The yield was 520.5 g (72.2%) at a purity of greater than 98.0% by 1H NMR.

Workup

  1. customThe organic phase was removed
  2. dry with materialdried over potassium carbonate
  3. distillationfractionally distilled (approx. 1 mbar, top temperature from 79 to 82° C.) by means of a Vigreux column (40 cm)
  4. customThe product was obtained as a colorless, low-viscosity oil

Sources & evidence

ORD record
ord-30441e9188ee410491001da6d20d30a7
Source dataset
uspto-grants-2010_06
Patent number
US07728137B2

Linked notes

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