Sulfuric Acid → 8-Bromochroman-3-ol

HRID 1464689Notes

Reaction equation

HRID 1464689 reaction equation
[OH:1]S(O)(=O)=O.[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Br:16])[CH:7]=[CH2:8]>O>[Br:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[O:9][CH2:6][CH:7]([OH:1])[CH2:8]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 913511-(Allyloxy)-2-bromobenzene

Product 1

HCID 190871458-Bromochroman-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Tl2O3 (2.38 g, 5.2 mmol) was added at room temperature to a mixture of H2SO4 (6.9 ml) and water (6.1 ml) and this mixture was stirred for 30 min and added to o-allyloxy-bromo-benzene (1.9 g, 8.92 mmol) and water was added (37 ml). The reaction mixture was stirred in 60° C. under Argon. The product was extracted with CH2Cl2 and the organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed under reduced pressure to give 1.34 g of a raw oil, which was chromatographed (SiO2 and ether as eluant). The fractions containing at least 85% purity of the product were pooled and the solvent was removed, yielding 310 mg of an oil. GC/MS showed M+ /M+2 at m/e=228.00(100%)/230.00(88%).

Workup

  1. additionwas added (37 ml)
  2. stirringThe reaction mixture was stirred in 60° C. under Argon
  3. extractionThe product was extracted with CH2Cl2
  4. washthe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto give 1.34 g of a raw oil, which
  9. customwas chromatographed (SiO2 and ether as eluant)
  10. additionThe fractions containing at least 85% purity of the product
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-fbe729a6cc454a84a7aa254394a56e05
Source dataset
uspto-grants-1994_04
Patent number
US05306830

Reaction notes

Loading…