Aluminium lithium hydride → (2,4-Difluoro-5-methylphenyl)methanol

HRID 2172641Notes

Reaction equation

HRID 2172641 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([F:11])=[CH:6][C:5]=1[F:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:12][C:5]1[CH:6]=[C:7]([F:11])[C:8]([CH3:10])=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 55264252HCID 55264252, compound

Product 1

HCID 45090665(2,4-Difluoro-5-methylphenyl)methanolYield 117.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,4-difluoro-5-methyl-benzoic acid methyl ester from Step A (1.0 g, 5.37 mmol) in tetrahydrofuran (10 mL), cooled to −78° C. using a dry ice/acetone bath, was added lithium aluminum hydride, 1.0M in tetrahydrofuran (10 mL, 10 mmol), in a dropwise manner. The solution was stirred for two hours. The reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution, allowed to warm to room temperature and was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a colorless liquid (1.0 g, quantitative yield).

Workup

  1. customThe reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5f583ada7034ca280d25d90fcbbd195
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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