Potassium Hydroxide → 2-(5-Chloro-2-fluorophenyl)ethan-1-ol

HRID 1810883Notes

Reaction equation

HRID 1810883 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 27737235-Chloro-2-fluorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 670764502-(5-Chloro-2-fluorophenyl)ethan-1-olYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 5 g (26.51 mmol) of 5-chloro-2-fluoro-phenylacetic acid in 60 ml of THF was added dropped to a suspension of 2.012 g (53.02 mmol) of lithium aluminium hydride in 26.5 ml of THF. 30 ml of THF were added, and the mixture was heated under reflux for 3 h. After cooling to 0° C., a solution of 929.7 mg (16.57 mmol) of potassium hydroxide in 4 ml of water was cautiously added and the mixture was stirred overnight at room temperature. The formed precipitate was filtered off with suction and washed with THF. The combined filtrates were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol 98:2) to give 3.8 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationThe formed precipitate was filtered off with suction
  4. washwashed with THF
  5. dry with materialThe combined filtrates were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography (DCM/methanol 98:2)

Sources & evidence

ORD record
ord-b7b514a452494994a9062388d24d9a19
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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