Sodium borohydride → N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide

HRID 1257162

Reaction equation

HRID 1257162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH:13]=[O:14].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 84784262N-(4-chloro-2-fluoro-3-formylphenyl)acetamide

Product 1

HCID 86713625N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of N-(4-chloro-2-fluoro-3-formylphenyl)acetamide (1.1 g, 5.10 mmol) in MeOH (10 mL) was treated portion-wise with sodium borohydride (0.193 g, 5.10 mmol), stirred at 0° C. for 0.5 h, then warmed to RT and concentrated to dryness. The residue was treated with water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide (1.05 g, 95% yield) as a white solid. MS (ESI) m/z: 218.0 [M+H]+.

Workup

  1. temperaturewarmed to RT
  2. concentrationconcentrated to dryness
  3. additionThe residue was treated with water
  4. extractionextracted with EtOAc (2×)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b0bb77f9e9324c4a86b06e5b1e90468a
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Linked notes

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