Hydrochloric Acid → HCID 58897793, compound

HRID 2357862Notes

Reaction equation

HRID 2357862 reaction equation
C1([Mg]Br)C=CC=CC=1.[Mg].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][CH2:21][C:22]2=O.Cl>C1COCC1.O.CCOCC>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:12]=1[CH2:22][CH:21]=[C:20]2[C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:18]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 987131-Indanone, 4-bromo-HCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 58897793HCID 58897793, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Under an argon atmosphere, to a solution of PhMgBr in THF [obtained from 7.60 g (0.312 mol) of magnesium turnings, 50.0 g (0.318 mmol) of bromobenzene, and 200 ml of THF], a solution of 43.9 g (0.208 mol) of 4-bromoindan-1-one in 400 ml of THF was added dropwise with vigorous stirring at −10° C. This mixture was stirred overnight at room temperature; and, then, 300 ml of ether was added. The resulting mixture was cooled to 0° C., and 200 ml of cold water and then 200 ml of 12 M HCl were added. The organic layer was separated; and the aqueous layer was extracted with 2×200 ml of dichloromethane. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 65 mm, 400 mm, eluant:hexanes) and then recrystallized from hexanes. Yield, 48.4 g (86%) of a white crystalline solid.

Workup

  1. stirringThis mixture was stirred overnight at room temperature
  2. temperatureThe resulting mixture was cooled to 0° C.
  3. customThe organic layer was separated
  4. extractionand the aqueous layer was extracted with 2×200 ml of dichloromethane
  5. extractionThe combined extract
  6. dry with materialwas dried over K2CO3
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 65 mm, 400 mm, eluant:hexanes)
  9. customrecrystallized from hexanes
  10. customYield

Sources & evidence

ORD record
ord-3c45d390a6dc4aedaed3c444ad95e811
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

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