Stannous chloride dihydrate → 3-(Benzyloxy)-5-bromoaniline

HRID 1010683Notes

Reaction equation

HRID 1010683 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 14784149HCID 14784149, compound

Product 1

HCID 578136263-(Benzyloxy)-5-bromoaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-benzyloxy-5-bromo-nitrobenzene (27.0 g, 87.60 mmol) in THF (800.0 mL) was added SnCl2.2H2O (99.0 g, 438.30 mmol) and the resulting reaction mixture was heated to reflux at 65° C. for 2 h. The reaction mass was then cooled to 0-5° C. and basified with a saturated solution of NaHCO3 till pH 8 and then extracted with EtOAc (3×1.0 L). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue thus obtained (23.60 g, 95%) was carried forward to the next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureThe reaction mass was then cooled to 0-5° C.
  4. extractionextracted with EtOAc (3×1.0 L)
  5. dry with materialThe combined organics was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained (23.60 g, 95%)
  8. customwas carried forward to the next step without further purification

Sources & evidence

ORD record
ord-88bd04f9dffe408a9ca528a8dd2b0eef
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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