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

HRID 626035
Notes
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Reaction equation

HRID 626035 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent

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-8a3960b2a6a64f0e8ec1507a97a59043
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309179B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes