Water → HCID 14954841, compound

HRID 643864Notes

Reaction equation

HRID 643864 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH:5]=[C:4]([Br:13])[C:3]=1[OH:14].[Sn].O>CC(O)=O.Cl>[Br:13][C:4]1[C:3]([OH:14])=[CH:2][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2

Participants

5

Reactant 3

HCID 962WaterHCID 5352426Tin atomHCID 14954840HCID 14954840, compound

Product 1

HCID 14954841HCID 14954841, compound

Reagents, catalysts & solvents 1

HCID 22641269Acetate-hydrochloric acidSolvent

Procedure

To a suspension of 1,3-dibromonaphthalene-2,7-diol (48.76 g, 153.34 mmol) (Helv. Chim. Acta, 78, pp. 1037-1066, 1995) in AcOH/HCl is added tin (17.48 g, 147.21 mmol) in portions. The mixture is stirred vigorously at room temperature for 1 h. The reaction forms a paste and is stirred for an additional 4 h, at which point it becomes mobile again. Stirring is continued overnight. The mixture is poured into water (1 L) and extracted with EtOAc. The organic layer is dried over MgSO4, filtered and concentrated to afford a sticky beige solid. The solid is triturated with DCM and filtered to afford 3-bromonaphthalene-2,7-diol as a fluffy beige solid.

Workup

  1. stirringis stirred for an additional 4 h, at which point it
  2. stirringStirring
  3. waitis continued overnight
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a sticky beige solid
  9. customThe solid is triturated with DCM
  10. filtrationfiltered

Sources & evidence

ORD record
ord-154fdabb831e48bc93c9dfaf9a92b832
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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