Sulfuric Acid → HCID 67053816, compound

HRID 2171733Notes

Reaction equation

HRID 2171733 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6]2.C1C(=O)N([Br:21])C(=O)C1.OS(O)(=O)=O>O>[Br:21][C:11]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:13])[CH3:12])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 221522852,3-Dihydro-5-methoxy-1,1-dimethyl-1H-indene

Product 1

HCID 67053816HCID 67053816, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-methoxy-1,1-dimethyl-indan (2.16 g, 12.25 mmol) (prepared following the procedures described in U.S. Pat. Appl. Publ., 2006100460) in water (120 ml), NBS (2.2 g, 12.3 mmol) was added. The reaction mixture was heated to 60° C. while stirring. Concentrated H2SO4 (1.3 ml, 40% aq. solution) was then added and stirring was continued for 5 hours. The reaction mixture was cooled to rt. The mixture was extracted with diethyl ether three times. The combined organic extract was washed with brine and dried (Na2SO4). Silica gel chromatography (ethyl acetate/heptane) provided 2.78 g (89%) of the title compound.

Workup

  1. customprepared
  2. stirringstirring
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionThe mixture was extracted with diethyl ether three times
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-84a60f795a234838a54cc47bf8638ed0
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

Loading…