Sodium borohydride → 2-(2-Fluoro-4-nitrophenyl)ethan-1-ol

HRID 1842954Notes

Reaction equation

HRID 1842954 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12](OC)=[O:13].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18369150Methyl 2-Fluoro-4-nitrophenylacetate

Product 1

HCID 866721582-(2-Fluoro-4-nitrophenyl)ethan-1-olYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of methyl 2-(2-fluoro-4-nitrophenyl)acetate (3.0 g, 14.0 mmol, 1.0 eq) in methanol (30 mL) was added NaBH4 (2.08 g, 36.3 mmol, 4.0 eg) at 0° C. and stirred at 70° C. for 16 h, then the methanol was evaporated and the residue was diluted with water (30 mL), the pH adjusted to being neutral with 2N HCl and the mixture extracted with EtOAc (50 mL×3). The organic layer was separated, washed with brine, dried over Na2SO4 and the solvent evaporated to yield 2-(2-fluoro-4-nitrophenyl)ethanol (2.0 g, 77%) as a viscous oil (TLC system: EtOAc/PE (3:7), Rf: 0.3).

Workup

  1. customthe methanol was evaporated
  2. additionthe residue was diluted with water (30 mL)
  3. extractionthe mixture extracted with EtOAc (50 mL×3)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-2fe3bc86216640c5a2587b8ddce146db
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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