Acetic Acid → 2-(Benzyloxy)-4-fluoroaniline

HRID 1289367Notes

Reaction equation

HRID 1289367 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1>C(OCC)(=O)C.[Fe]>[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 167713362-(Benzyloxy)-4-fluoroanilineYield 70.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
76 °C

Procedure

To a mixture of iron powder (90.36 g, 1.62 mol) and acetic acid (10%, 400 mL) at 80° C. was added a solution of the title compound of Step A (40 g, 0.162 mol) in ethyl acetate (200 mL) dropwise with vigorous stirring. The reaction mixture was stirred further at 76° C. for 1 h. After the reaction was complete, the hot reaction mixture was filtered through Celite® (200 g) and the filter cake was washed with ethyl acetate (1000 mL). The filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL), dried (MgSO4) and concentrated to give the crude product. The product was purified by flash chromatography to give 24.76 g of the title compound of Step B. 1H NMR (CDCl3, 400 MHz): δ7.41 (m,5H), 6.60 (m,3H), 5.04 (s,2H).

Workup

  1. filtrationthe hot reaction mixture was filtered through Celite® (200 g)
  2. washthe filter cake was washed with ethyl acetate (1000 mL)
  3. washThe filtrate was washed with water (3×200 mL), sodium bicarbonate solution (5%, 3×200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-08479fc24d0343a9b5cdf9355c466806
Source dataset
uspto-grants-1998_05
Patent number
US05750471

Reaction notes

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