Ethanol → 4-(Benzyloxy)-2-fluoroaniline

HRID 1407146Notes

Reaction equation

HRID 1407146 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([F:26])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1COCC1.CCO>O>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([F:26])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Product 1

HCID 114998094-(Benzyloxy)-2-fluoroanilineYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of Na2S2O4 (34.8 g, 200 mmol) in H2O (200 mL) was added to a mixture of 4-(benzyloxy)-2-fluoro-1-nitrobenzene (16.0 g, 64.7 mmol), THF (150 mL), and EtOH (150 mL), and the mixture was stirred for 30 min at room temperature. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography eluting with hexane/AcOEt (1/1) to give the title compound (5.84 g, 42% yield) as a light brown oil: 1H NMR (300 MHz, CDCl3): δ ppm 3.42 (2H, brs), 4.97 (2H, s), 6.60 (1H, ddd, J=1.1, 2.6, 8.7 Hz), 6.67-6.74 (2H, m), 7.28-7.43 (5H, m).

Workup

  1. extractionextracted with AcOEt
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography
  6. washeluting with hexane/AcOEt (1/1)

Sources & evidence

ORD record
ord-b18c65fa7f2d4a4a9712e64c5ee67ed3
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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