Dichloromethane → 2-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561485Notes

Reaction equation

HRID 561485 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6]([CH:8]1[CH2:10][CH:9]1[C:11]#[N:12])=[O:7].ClCCl>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[CH:6]([OH:7])[CH:8]1[CH2:10][CH:9]1[C:11]#[N:12]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 583925012-(2-Chloro-4-fluorobenzoyl)cyclopropanecarbonitrile

Product 1

HCID 583924412-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

409 mg (10.8 mmol) of sodium borohydride were added to 2.20 g (9.84 mmol) of the compound from Example 127A in 180 ml of ethanol and 60 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to dichloromethane, the phases were separated, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 1.52 g (69% of theory) of a mixture of the diastereomers of the title compound.

Workup

  1. customthe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Sources & evidence

ORD record
ord-3f7694c970b54369b45e3665c2a5eb88
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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