Ammonium Chloride → 8-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 2353408Notes

Reaction equation

HRID 2353408 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].[Mg].[O:12]1[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>O1CCCC1>[F:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[C:19]1([OH:22])[CH2:20][CH2:21][C:16]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

Product 1

HCID 574243598-(2,4,5-Trifluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

A three neck flask (2 L) under an atmosphere of nitrogen with Mg turnings (9.8 g) was stirred for 15 min and tetrahydrofuran (90 mL) was added and stirring continued for an additional 15 min. 1-Bromo-2,4,5-trifluorobenzene (85 g) was dissolved in tetrahydrofuran (340 mL). A portion of this solution (75 mL) was added to the stirred magnesium turnings and then heated to 50° C. The rest of the solution was added and stirring continued at the same temperature for an additional 1 h. The reaction mixture was cooled to 40° C., a solution of 1,4-dioxaspiro[4.5]decan-8-one (57.3 g) in tetrahydrofuran (275 mL) was added, and stirring continued for 10 h. The reaction mixture was poured into saturated aqueous ammonium chloride solution (970 mL) and extracted with toluene (700 mL). The organic layer was washed with water (3×700 mL), dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound as a red-orange oil which was used in the next step without further purification.

Workup

  1. additionThe rest of the solution was added
  2. stirringstirring
  3. waitcontinued at the same temperature for an additional 1 h
  4. temperatureThe reaction mixture was cooled to 40° C.
  5. stirringstirring
  6. waitcontinued for 10 h
  7. extractionextracted with toluene (700 mL)
  8. washThe organic layer was washed with water (3×700 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-ee287a1eda88406aafdf0a4fa836889d
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

Loading…