Water → HCID 57678436, compound

HRID 491509Notes

Reaction equation

HRID 491509 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([O:13]C)[C:5]([CH:10]([CH3:12])[CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.B(Br)(Br)Br.O>ClCCl>[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]([CH3:12])[CH3:11])=[C:4]([OH:13])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 57678424HCID 57678424, compound

Product 1

HCID 57678436HCID 57678436, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-Iodo-2-isopropyl-1,3-dimethoxy-benzene (805 mg, 2.63 mmol) in anhydrous dichloromethane (26 mL) at 0° C. was added boron tribromide (2.63 mL, 2.63 mmol) 1M in dichloromethane), maintaining the temperature of the reaction at 0° C. during the addition. After stirring at room temperature for 18 hours, water (10 mL) was slowly added to the reaction. After stirring 30 minutes, the dichloromethane layer was collected, dried using anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography eluting with 90/10 hexane/ethyl acetate yielded 5-Iodo-2-isopropyl-3-methoxy-phenol (612 mg, 80%) as an oil, MS (M+H)=293.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction at 0° C.
  3. additionduring the addition
  4. stirringAfter stirring 30 minutes
  5. customthe dichloromethane layer was collected
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification of the residue by silica gel column chromatography
  10. washeluting with 90/10 hexane/ethyl acetate

Sources & evidence

ORD record
ord-79b38f4806a740dea10d73d6f9da941b
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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