Sodium borohydride → 3-Amino-4-fluoro-α-methylbenzenemethanol

HRID 2307432Notes

Reaction equation

HRID 2307432 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>CO.C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 106069533'-Amino-4'-fluoroacetophenone

Product 1

HCID 226055413-Amino-4-fluoro-α-methylbenzenemethanolYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-amino-4-fluorophenyl)-ethanone (3 g) in a mixture of MeOH (20 mL) and CH2Cl2 (20 mL) was added in portions NaBH4 (1520 mg) at 0° C. After stirring for 0.5 hours, the reaction mixture was quenched with saturated NH4Cl solution and most of the solvent was removed in vacuo. The residue was extracted with CH2Cl2, and the combined organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane) to give 2.9 g of the title compound as an oil.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl solution and most of the solvent
  2. customwas removed in vacuo
  3. extractionThe residue was extracted with CH2Cl2
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-85cfe6ad145f4b0392d1dd6949b269fb
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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