Water → 6-Iodonaphthalen-2-ol

HRID 1254183Notes

Reaction equation

HRID 1254183 reaction equation
B(Br)(Br)Br.[I:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16]C)[CH:12]=2)[CH:7]=1.O>ClCCl>[I:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 3490672-Iodo-6-methoxynaphthalene

Product 1

HCID 135288166-Iodonaphthalen-2-olYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

BBr3 (102 g, 407 mmol) is added dropwise over 30 min to a slightly cloudy solution/suspension of 2-iodo-6-methoxy-naphthalene (45.4 g, 160 mmol) in dichloromethane (dried over 3 {acute over (Å)} molecular sieves) (1 L) at −8° C. The mixture is warmed to 20° C. and stirred at this temp for 1.5 h. Water (400 mL) is carefully added (slow dropwise addition at the start) and the biphasic mixture vigorously stirred for 20 min. The layers are separated and the aqueous layer extracted with dichloromethane (250 mL) with additional water (400 mL) being added. The combined organic fractions are washed with water (500 mL), dried (Na2SO4), filtered and solvent removed in vacuo to give a colourless solid with silvery purple patches (44.7 g). This is recrystallised from IMS/water (initially dissolved in 100 mL IMS) washing with water and dried in a vacuum oven to give an off-white solid (40.3 g, 94%).

Workup

  1. additionslow dropwise addition at the start) and the biphasic mixture
  2. stirringvigorously stirred for 20 min
  3. customThe layers are separated
  4. extractionthe aqueous layer extracted with dichloromethane (250 mL) with additional water (400 mL)
  5. additionbeing added
  6. washThe combined organic fractions are washed with water (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customsolvent removed in vacuo
  10. customto give a colourless solid with silvery purple patches (44.7 g)
  11. customThis is recrystallised from IMS/water (
  12. dissolutioninitially dissolved in 100 mL IMS)
  13. washwashing with water
  14. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c5b3ac57170b49168a6fd10b3b65e1b7
Source dataset
uspto-grants-2013_06
Patent number
US08455563B2

Reaction notes

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