Acetone → 2-(5-Fluoro-2-methoxyphenyl)propan-2-ol

HRID 1061640Notes

Reaction equation

HRID 1061640 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1362922-Bromo-4-fluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 222848882-(5-Fluoro-2-methoxyphenyl)propan-2-olYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2-bromo-4-fluoro anisole (4.1 g, 20 mmol) in anhydrous THF (40 mL) cooled to −78° C. and maintained under an atmosphere of argon was added n-butyl lithium (8.8 mL of 2.5 M solution in hexanes, 22 mmol). After stirring at −78° C. for 45 minutes, the reaction mixture was treated with anhydrous acetone (5 mL). After 15 minutes, the reaction mixture was quenched with a saturated solution of ammonium chloride and extracted with three 50 mL portions of methylene chloride. Combined extracts were washed with three 25 mL portions of water, dried over anhydrous sodium sulfate, and the solvent was evaporated to give 2-(5-fluoro-2-methoxyphenyl)propan-2-ol as a light brown thick oil (85% yield) which solidified on standing. The crude product was used for the next reaction without further purification.

Workup

  1. temperaturemaintained under an atmosphere of argon
  2. waitAfter 15 minutes
  3. customthe reaction mixture was quenched with a saturated solution of ammonium chloride
  4. extractionextracted with three 50 mL portions of methylene chloride
  5. washCombined extracts were washed with three 25 mL portions of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1bcf7d8201ab4a4598877841ced1b3ed
Source dataset
uspto-grants-2005_11
Patent number
US06960581B2

Reaction notes

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