Sulfuric Acid → 6-Bromo-1,1-dimethyl-1,3-dihydro-2-benzofuran

HRID 2105067Notes

Reaction equation

HRID 2105067 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:17][OH:18])=[C:11]([C:13](O)([CH3:15])[CH3:14])[CH:12]=1>O1CCOCC1.O>[Br:6][C:7]1[CH:12]=[C:11]2[C:10]([CH2:17][O:18][C:13]2([CH3:14])[CH3:15])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 578036042-(5-Bromo-2-(hydroxymethyl)phenyl)propan-2-ol

Product 1

HCID 578038426-Bromo-1,1-dimethyl-1,3-dihydro-2-benzofuranYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

H2SO4 (0.4 mL conc, 1.6 mL H2O) was added to a solution of Intermediate 388.1 (0.25 g, 1.02 mmol) in dioxane (2 mL). The mixture was stirred at 60° C., diluted with H2O (10 mL), extracted with hexanes (2×25 mL). The organics were combined, washed with brine, dried (Na2SO4) and concentrated to yield 200 mg of Intermediate 388.2 as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (s, 6H) 5.01 (s, 2H) 6.98 (m, 1H) 7.32 (m, 1H) 7.37 (m, 1H).

Workup

  1. extractionextracted with hexanes (2×25 mL)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d7ffb09ee264047859fe3979de67bf3
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…