Hydrochloric Acid → 4-(2-Benzyloxy-4-ethylphenoxy)-3-fluoroaniline

HRID 1023945Notes

Reaction equation

HRID 1023945 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl.Cl.[OH-].[Na+]>CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=1[F:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 591912382-(Benzyloxy)-4-ethyl-1-(2-fluoro-4-nitrophenoxy)benzene

Product 1

HCID 591912224-(2-Benzyloxy-4-ethylphenoxy)-3-fluoroanilineYield 68.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-(benzyloxy)-4-ethyl-1-(2-fluoro-4-nitro phenoxy)benzene (25 g; 68 mmol) in ether (86 mL), under argon cooled to 0° C., was added a suspension of tin dichloride (153 g; 801 mmol) in HCl (50 mL; 2 mol). The mixture was allowed to warm up to room temperature overnight, then a 10% NaOH solution was added dropwise. The resulting mixture was extracted with ethyl acetate (5*400 mL). Combined organic phases were washed with water (400 mL) and brine, then dried over Na2SO4 and concentrated. The residue was purified on silica gel (ethyl acetate/cyclohexane 1:9) to yield the title compound as a light brown solid (15.8 g; 68.8%)

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with ethyl acetate (5*400 mL)
  3. washCombined organic phases were washed with water (400 mL) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (ethyl acetate/cyclohexane 1:9)

Sources & evidence

ORD record
ord-4b21beee61f849d9a69faa14b2020b96
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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