Sodium borohydride → (2-Fluoro-4-nitrophenyl)methanol

HRID 64336

Reaction equation

HRID 64336 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 45629192-Fluoro-4-nitrobenzaldehyde

Product 1

HCID 17981733(2-Fluoro-4-nitrophenyl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitrobenzaldehyde (1.0 g, 5.92 mmol) in CH3OH (10 mL) was added NaBH4 (814 mg, 22 mmol). After stirring at RT for 15 min, the mixture was concentrated. The residue was partitioned between 100 mL of EA and 100 mL of brine. The combined organic layers were washed with brine (100 mL×2), dried over Na2SO4, and concentrated to afford 1.0 g of (2-fluoro-4-nitrophenyl) methanol (99%) as a red solid. MS (ESI) m/e [M+1]+ 172.0.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between 100 mL of EA and 100 mL of brine
  3. washThe combined organic layers were washed with brine (100 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf1bd06299bd4455957dcef8c4381f7e
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Linked notes

Loading…