Hydrochloric Acid → HCID 59832534, compound

HRID 269447Notes

Reaction equation

HRID 269447 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([CH3:15])=[CH:11][CH:12]=2)[C:7]1=[O:16].[Br:17]Br.Cl>ClCCl>[Br:17][C:12]1[CH:11]=[C:10]([CH3:15])[CH:9]=[C:8]2[C:13]=1[CH2:14][CH:6]([CH3:5])[C:7]2=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 115934772,6-dimethyl-2,3-dihydroinden-1-one

Product 1

HCID 59832534HCID 59832534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of 334 g (2.50 mol) of anhydrous AlCl3 (powder) in 400 ml of dry dichloromethane, a solution of 160 g (1.00 mol) of 2,6-dimethylindan-1-one in 200 ml of dichloromethane was added dropwise while vigorously stirring for 30 min at 0° C. This mixture was stirred for 1 h at ambient temperature, and then a solution of 51.6 ml (161 g, 1.01 mol) of bromine in 800 ml of dichloromethane was added while vigorously stirring for 2 h. The resulting mixture was stirred for 12 h and then poured on 700 cm3 of ice. The mixture was acidified by saturated HCl to pH 1, the organic layer was separated, and the aqueous layer was extracted with 3×350 ml of dichloromethane. The combined organic fractions were dried over K2CO3 and then evaporated to dryness. From the residue, 71.0 g of the starting indanone was distilled off in vacuum (bp 89-91 mm Hg), and the solid material left in the rectification flask was recrystallized from 600 ml of hot hexanes. Crystals that precipitated at room temperature were collected. The pure title product was then isolated by flash chromatography on Silica Gel 60 (40-63 um, d 50 mm, l 1200 mm, eluent: hexanes-dichloromethane, 10:1, vol.). Yield 44.0 g (18%).

Workup

  1. stirringThis mixture was stirred for 1 h at ambient temperature
  2. stirringwhile vigorously stirring for 2 h
  3. stirringThe resulting mixture was stirred for 12 h
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with 3×350 ml of dichloromethane
  6. dry with materialThe combined organic fractions were dried over K2CO3
  7. customevaporated to dryness
  8. distillationFrom the residue, 71.0 g of the starting indanone was distilled off in vacuum (bp 89-91 mm Hg)
  9. waitthe solid material left in the rectification flask
  10. customwas recrystallized from 600 ml of hot hexanes
  11. customCrystals that precipitated at room temperature
  12. customwere collected

Sources & evidence

ORD record
ord-6414386a08eb44a1a60ecea3661e2dd7
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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