Potassium Carbonate → (R)-5-Bromo-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

HRID 854173Notes

Reaction equation

HRID 854173 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:29])([CH3:28])[CH2:12][C@:13]([CH2:19]SC2C=CC(C)=CC=2)([OH:18])[C:14]([F:17])([F:16])[F:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.F[B-](F)(F)F.C[O+](C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:28])([CH3:29])[CH2:12][C@:13]2([C:14]([F:17])([F:15])[F:16])[CH2:19][O:18]2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 69415185(S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Product 1

HCID 11508851(R)-5-Bromo-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuranYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol (11.1 g, 22.6 mmol) in 75 mL of anhydrous dichloromethane was added trimethyloxonium tetrafluoroborate (5.18 g, 35.0 mmol). The resulting suspension was stirred at room temperature for 4.5 hours. A solution of potassium carbonate (9.40 g, 68.0 mmol) in 75 mL of water was then added. After 13 hours, the reaction mixture was poured into 200 mL of saturated aqueous sodium bicarbonate solution and extracted with three 300 mL portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography with silica gel (eluted with 0%-2% EtOAc-hexanes) afforded the title compound as a clear oil (7.84 g, 95%).

Workup

  1. waitAfter 13 hours
  2. extractionextracted with three 300 mL portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography with silica gel (eluted with 0%-2% EtOAc-hexanes)

Sources & evidence

ORD record
ord-44c048afc0704ca4a4afff8a47a82c86
Source dataset
uspto-grants-2007_08
Patent number
US07256300B2

Reaction notes

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